Pharmaceutical compositions and treatment methods - 8

Abstract

The invention provides compositions comprising formula 1 steroids, e.g., 16α-bromo-3β-hydroxy-5α-androstan-17-one hemihydrate and one or more excipients, typically wherein the composition comprises less than about 3% water. The compositions are useful to make improved pharmaceutical formulations. The invention also provides methods of intermittent dosing of steroid compounds such as analogs of 16α-bromo-3β-hydroxy-5α-androstan-17-one and compositions useful in such dosing regimens. The invention further provides compositions and methods to inhibit pathogen (viral) replication, ameliorate symptoms associated with immune dysregulation and to modulate immune responses in a subject using certain steroids and steroid analogs. The invention also provides methods to make and use these immunomodulatory compositions and formulations.

1 . A composition comprising one or more excipients and a compound having the structure  
       
         
           
           
               
               
           
         
       
       wherein 
 R 2  is —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 3  is —H, —OH, —OR PR , —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 5  and R 6  independently are —H, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl;  
 R 7  is —CHR 10 —, —CHR 10 —CHR 10 —, —CHR 10 —CHR 10 —CHR 10 —, —CHR 10 —O—CHR 10 —, —CHR 10 —S—CHR 10 —, —CHR 10 —NR PR —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, wherein R 10  independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 8  is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 8  is absent, leaving a 5-membered ring, wherein R 10  independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 9  is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHRO— —NR PR — or —NR PR —CHR 10 —, or R 9  is absent, leaving a 5-membered ring, wherein R 10  independently are —H, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, a thioester, an amide, an amino acid, a peptide, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide, a nucleoside, a nucleotide, an oligonucleotide or a polymer;  
 R PR  independently or together are —H, or protecting groups;  
 R 13  independently are C 1 -C 6  alkyl; and  
 (a) R 1  is —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer; and  
 one R 4  is a carbonate and the other R 4  is —H, —OH, —OR PR , —SH, —SR PR , —N 3 , —NH 2 , —N(R PR ) 2 , —CN, —NO 2 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer; or  
 (b) R 1  is a carbonate; and  
 R 4  independently are —H, —OH, —OR PR , —SR, SR PR , —N 3 , —NH 2 , —N(R PR ) 2 , —CN, —NO 2 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer, provided that R 4  are not both —H.  
 
     
     
         2 . The composition of  claim 1  wherein R 1  is —OR PR , —SR PR , NH(R PR ) 2 , ═O or ═S, R 2  is —H, —OR PR , —SR PR , —NH(R PR ) 2 , ═O, ═S, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, R 3  is —H, —F, —Cl, —Br, —I, —OR PR , —SR PR , —NH(R PR ) 2 , ═O, ═S, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl, one R 4  is a carbonate and the other R 4  is is —H, acyl, thioacyl, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl.  
     
     
         3 . The composition of  claim 2  wherein the carbonate is —O—C(O)—O—NHC(CH 3 )H—CO 2 H, —O—C(O)—O—NHCH 2 —CO 2 H, —O—C(O)—O—NH(CH 2 C 6 H 5 )H—CO 2 H, —O—C(O)—O—CH 3 , —O—C(O)—O—CH 2 CH 3 , —O—C(O)—O—C 3 H 7 , —O—C(O)—O—C 4 H 9 , —O—C(O)—O—C 6 H 13 , —O—C(O)—O—C 6 H 5 , —O—C(O)—O—C 6 H 4 OH, —O—C(O)—O—C 6 H 4 OCH 3 , —O—C(O)—O—C 6 H 4 OCH 2 CH 3  or —O—C(O)—O—C 6 H 4 F.  
     
     
         4 . The composition of  claim 1  wherein R 1  is a carbonate, R 2  is —H, —OR PR , —SR PR , —NH(R PR ) 2 , ═O, ═S, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, R 3  is —H, —F, —Cl, —Br, —I, —OR PR , —SR PR , NH(R PR ) 2 , ═O, ═S, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl, one R 4  is OFR PR , SR PR , —NH(R PR ) 2 , ═O, ═S, an ester, an ether, a thioester, a thioether, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer and the other R 4  is is —H, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl.  
     
     
         5 . The composition of  claim 1  having the structure  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         6 . The composition of  claim 1  wherein R 2  is —H and the composition is a formulation.  
     
     
         7 . The formulation of  claim 5  wherein R 2  is —H and the composition is a formulation.  
     
     
         8 . The composition of  claim 1  wherein the compound has the structure  
       
         
           
           
               
               
           
         
       
       and the composition is a formulation.  
     
     
         9 . The formulation of  claim 8  wherein R 1  is —OH, —OR PR , an ester or an ether, R 2  is —H, —OH or ═O, R 3  is —H, —OH, ═O, —F, —Cl, —Br or —I, R 4  is —O—C(O)—O—NHC(CH 3 )H—CO 2 H, —O—C(O)—O—NHCH 2 —CO 2 H, —O—C(O)—O—NH(CH 2 C 6 H 5 )H—CO 2 H, —O—C(O)—O—CH 3 , —O—C(O)—O—CH 2 CH 3 , —O—C(O)—O—C 3 H 7 , —O—C(O)—O—C 4 H 9 , —O—C(O)—O—C 6 H 13 , —O—C(O)—O—C 6 H 5 , —O—C(O)—O—C 6 H 4 OH, —O—C(O)—O—C 6 H 4 OCH 3 , —O—C(O)—O—C 6 H 4 OCH 2 CH 3  or —O—C(O)—O—C 6 H 4 F, R 5  is —H, —CH 3  or —CH 2 OH, R 6  is —H, —CH 3  or —CH 2 OH, R 7  is —CH 2 — or —CH 2 —CH 2 —, R 8  is —CH 2 —, —NH— or —O— and R 9  is —CH 2 —, —NH— or —O—.  
     
     
         10 . The formulation of  claim 9  wherein R 1  is —O—C(O)—CH 3 , —O—C(O)—C 2 H 5 , —OR PR  wherein R PR  is methoxymethyl or methylthiomethyl, R 2  and R 3  are —H, R 5  is —CH 3 , and R 6  is —H or —CH 3 , and R 7 , R 8  and R 9  are —CH 2 —.  
     
     
         11 . The formulation of  claim 8  wherein 
 R 1  is —H, —CH 3 , —OH, ═O, —SH, ═S, —OCH 3 , —O—S(O)(O)—O—Na + , —O—S(O)(O)—OC 2 H 5 , —OC(O)C(CH 3 ) 3 , —O—C(O)—CH 2 CH 2 CH 2 CH 3 , —O—C(O)—CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 , —O—C(O)—CH 2 CH 2 OCH 2 CH 3 , —O—C(O)—CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 3 , —O—C(O)—CH 2 CH 2 CH 2 CH 2 OCH 2 CH 3 , —O—C(O)—CH 2 CH 2 OCH 2 CH 2 CH 2 CH 3 , —O—C 6 H 4 Cl, —O—C 6 H 3 F 2 , —O—C 6 H 4 —O(CH 2 ) 2 —O—CH 2 CH 3 , —O—C 6 H 4 —C(O)O(CH 2 ) 0-9 CH 3 , —O—P(O)(O)—OCH 2 CH(CH 3 )CH 3  (—O—P(O)(O)—OCH 2 CH(CH 3 )CH 3 , —O—P(O)(O)—OCH 2 CH 2 CH 2 CH 2 CH 3 , —O—P(O)(O)—OCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 , —O—P(O)(O)—OCH 2 CH 2 CH(CH 2 CH 2 )CH 3 , —O—CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 , —O—C 2 H 5 , —O—CH 2 CH 2 CH 3 , —O—CH 2 CH 2 CH 2 CH 3 , —O—CH(CH 3 )CHCH 3 , —O—C(CH 3 ) 3 , —O—(CH 2 ) 4 CH 3 , —O—C(O)—NH 2 , —O—C(O)—NHCH 3 , —O—C(O)—NHC 2 H 5 , —O—C(O)—NHCH 2 CH 2 CH 3 , —O—C(O)—NHCH 2 CH 2 OCH 2 CH 3 , —O—C(O)—CH 3 , —O—C(O)—C 2 H 5 , —O—C(O)—CH 2 CH 2 CH 3 , —O—C(O)—CH 2 CH 2 CH 2 CH 3 , —O—CH 2 C 6 H 5 , —O—CH 2 C 6 H 5 , —O—CH 2 C 6 H 4 OCH 3 , —O—CH 2 C 6 H 4 OCH 3 , —O—CH 2 C 6 H 4 F, —O—CH 2 C 6 H 4 F, —O—CH 2 C 6 H 3 (OCH 3 ) 2 , —O—CH 2 C 6 H 3 (OCH 3 ) 2 , —O—CH 2 C 6 H 4 OCH 2 CH 3 , —O—CH 2 C 6 H 4 OCH 2 CH 3 , —O—C(O)—CH 2 CH 2 NH 2 , —O—C(O)—CH 2 CH 2 CH 2 NH 2 , —O—C(O)—CH 2 OH, —O—C(O)—CH 2 CH 2 OH, —O—C(O)—CH 2 CH 2 CH 2 OH, —O—C(O)—CH 2 SH, —O—C(O)—CH 2 CH 2 SH, —O—C(O)—CH 2 CH 2 CH 2 SH, —O—S(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 2 H 5 , —O—P(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 2 H 5 , —O—C(O)—C4 alkyl-NH 2 , —O—C(O)—C6 alkyl-NH 2 , —O—C(O)—C8 alkyl-NH 2 , —O—C(O)—C4 alkyl-OH, —O—C(O)—C6 alkyl-OH, —O—C(O)—C8 alkyl-OH, —O—S(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 3 H 7 , —O—P(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 3 H 7 , —O—S(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 4 H 9 , —O—P(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 4 H 9 , —O—S(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 6 H 13 , —O—P(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 6 H 13 , —O—S(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 8 H 17 , —O—P(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—C 8 H 17 , —O—S(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—CH 2 C 5 H 10 OH, —O—P(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—CH 2 C 5 H 10 OH, —O—S(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—CH 2 C 3 H 6 OH, —O—P(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—CH 2 C 3 H 6 OH, —O—S(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—CH 2 C 7 H 14 OH or —O—P(O)(O)—O—CH 2 —CH(O—C(O)—OH)—CH 2 —O—C(O)—CH 2 C 7 H 14 OH    R 2  is —H, —OH, ═O, —CH 3 , —OCH 3 , —OC 2 H 5 , —OCH 2 CH 2 CH 3 , —OCH 2 CH 2 CH 2 CH 3 ,    R 3  is —H, —OH, ═O, —F, —Cl, —Br, —I, —O—C(O)—CH 3 , —O—C(O)—CH 2 CH 3 , —O—C(O)—CH 2 CH 2 CH 3 , 
 R 4  is —O—C(O)—O—NHC(CH 3 )H—CO 2 H, —O—C(O)—O—NHCH 2 —CO 2 H, —O—C(O)—O—NH(CH 2 C 6 H 5 )H—CO 2 H, —O—C(O)—O—CH 3 , —O—C(O)—O—CH 2 CH 3 , —O—C(O)—O—C 3 H 7 , —O—C(O)—O—C 4 H 9 , —O—C(O)—O—C 6 H 13 , —O—C(O)—O—C 6 H 5 , —O—C(O)—O—C 6 H 4 OH, —O—C(O)—O—C 6 H 4 OCH 3 , —O—C(O)—O—C 6 H 4 OCH 2 CH 3  or —O—C(O)—O—C 6 H 4 F;  
 R 5  is —H, —CH 3  or —CH 2 OH;  
 R 6  is —H, —CH 3  or —CH 2 OH;  
 R 7  is —CH 2 —, —CH 2 —CH 2 —, —O—, —S— or —NH—;  
 R 8  is —CH 2 —, —O—, —S—, —NH— or is absent; and  
 R 9  is —CH 2 —, ═CH—, —O—, —S—, —NH—, ═N— or is absent.  
   
     
     
         13 . The composition of  claim 1  wherein the compound has the structure  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         14 . The composition of  claim 13  wherein R 1  is —OH, —OR PR , an ester, a thioester, an ether, a thioether or a polymer, R 2  is —H, —OH or ═O, R 3  is —H, —OH, ═O, —F, —Cl, —Br or —I and R 4  is —O—C(O)—O—NHC(CH 3 )H—CO 2 H, —O—C(O)—O—NHCH 2 —CO 2 H, —O—C(O)—O—NH(CH 2 C 6 H 5 )H—CO 2 H, —O—C(O)—O—CH 3 , —O—C(O)—O—CH 2 CH 3 , —O—C(O)—O—C 3 H 7 , —O—C(O)—O—C 4 H 9 , —O—C(O)—O—C 6 H 13 , —O—C(O)—O—C 6 H 5 , —O—C(O)—O—C 6 H 4 OH, —O—C(O)—O—C 6 H 4 OCH 3 , —O—C(O)—O—C 6 H 4 OCH 2 CH 3  or —O—C(O)—O—C 6 H 4 F and the composition is a formulation.  
     
     
         15 . The formulation of  claim 14  wherein —O—C(O)—CH 3 , —O—C(O)—C 2 H 5 , —OR PR  where R PR  is methoxymethyl or methylthiomethyl, R 5  is —H, —CH 3  or —CH 2 OH, R 6  is —H, —CH 3  or —CH 2 OH, R 7  is —CH 2 — or —CH 2 —CH 2 —, R 8  is —CH 2 —, —NH—, —S— or —O— and R 9  is —CH 2 —, —NH—, —S— or —O—.  
     
     
         16 . The composition of  claim 1  wherein the composition contains 
 (1) 3α,17β-dihydroxy-5α-androst-1-ene, 3β,17β-dihydroxy-5α-androst-1-ene, 3α,17β-dihydroxy-19-nor-5α-androst-1-ene, 3α,17β-dihydroxy-19-nor-5α-androst-1-ene, 3α,17β-dihydroxy-19-nor-5α-androst-1-ene, 3-oxo-5α-androst-1-ene-17β-methylcarbonate, 3-oxo-5α-androst-1-ene-17β-ethylcarbonate, 3-oxo-5α-androst-1-ene-17β-propylcarbonate, 3-oxo-5α-androst-1-ene-17β-butylcarbonate, 3-oxo-5α-androst-1-ene-17β-hexylcarbonate, 3-oxo-5α-androst-1-ene-17β-phenylcarbonate, 3α-hydroxy-5α-androst-1-ene-17β-methylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-methylcarbonate, 3-hydroxy-5α-androst-1-ene-17β-ethylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-ethylcarbonate, 3-hydroxy-5α-androst-1-ene-17β-propylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-propylcarbonate, 3α-hydroxy-5α-androst-1-ene-17β-butylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-butylcarbonate, 3α-hydroxy-5α-androst-1-ene-17β-hexylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-hexylcarbonate, 3α-hydroxy-5α-androst-1-ene-17β-phenylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-phenylcarbonate, 3α-methoxy-5α-androst-1-ene-17β-methylcarbonate, 3β-methoxy-5α-androst-1-ene-17β-methylcarbonate, 3α-methoxy-5α-androst-1-ene-17β-ethylcarbonate, 3β-methoxy-5α-androst-1-ene-17β-ethylcarbonate, 3α-methoxy-5α-androst-1-ene-17β-propylcarbonate, 3β-methoxy-5α-androst-1-ene-17β-propylcarbonate, 3α-methoxy-5α-androst-1-ene-17β-butylcarbonate, 3β-methoxy-5α-androst-1-ene-17β-butylcarbonate, 3-methoxy-5α-androst-1-ene-17β-hexylcarbonate, 3β-methoxy-5α-androst-1-ene-17β-hexylcarbonate, 3α-methoxy-5α-androst-1-ene-17β-phenylcarbonate, 3β-methoxy-5α-androst-1-ene-17β-phenylcarbonate, 3α-ethoxy-5α-androst-1-ene-17β-methylcarbonate, 3β-ethoxy-5α-androst-1-ene-17β-methylcarbonate, 3α-ethoxy-5α-androst-1-ene-17β-ethylcarbonate, 3β-ethoxy-5α-androst-1-ene-17β-ethylcarbonate, 3α-ethoxy-5α-androst-1-ene-17β-propylcarbonate, 3β-ethoxy-5α-androst-1-ene-17β-propylcarbonate, 3α-ethoxy-5α-androst-1-ene-17β-butylcarbonate, 3β-ethoxy-5α-androst-1-ene-17β-butylcarbonate, 3α-ethoxy-5α-androst-1-ene-17β-hexylcarbonate, 3β-ethoxy-5α-androst-1-ene-17β-hexylcarbonate, 3α-ethoxy-5α-androst-1-ene-17β-phenylcarbonate, 3β-ethoxy-5α-androst-1-ene-17β-phenylcarbonate or an analog of any of these compounds having a hydroxyl at the 3-position, where the analog is a hydroxyl ester or a hydroxyl ether optionally selected from the group consisting of —O—C(O)—CH 3 , —O—C(O)—CF 3 , —O—C(O)—C 2 H 5 , —OC 3 H 7  or —OC 4 H 9 ; and/or    (2) 3α,17β-dihydroxyandrost-4-ene, 3β,17β-dihydroxyandrost-4-ene, 3α,17β-dihydroxy-19-norandrost-4-ene, 3α,17β-dihydroxy-19-norandrost-4-ene, 3α,17β-dihydroxy-19-nor-5α-androst-4-ene, 3-oxo-androst-4-ene-17β-methylcarbonate, 3-oxo-androst-4-ene-17β-ethylcarbonate, 3-oxo-androst-4-ene-17β-propylcarbonate, 3-oxo-androst-4-ene-17β-butylcarbonate, 3-oxo-androst-4-ene-17β-hexylcarbonate, 3-oxo-androst-4-ene-17β-phenylcarbonate, 3α-hydroxyandrost-4-ene-17β-methylcarbonate, 3β-hydroxyandrost-4-ene-17β-methylcarbonate, 3α-hydroxyandrost-4-ene-17β-ethylcarbonate, 3β-hydroxyandrost-4-ene-17β-ethylcarbonate, 3α-hydroxyandrost-4-ene-17β-propylcarbonate, 3β-hydroxyandrost-4-ene-17β-propylcarbonate, 3α-hydroxyandrost-4-ene-17β-butylcarbonate, 3β-hydroxyandrost-4-ene-17β-butylcarbonate, 3α-hydroxyandrost-4-ene-17β-hexylcarbonate, 3β-hydroxyandrost-4-ene-17β-hexylcarbonate, 3α-hydroxyandrost-4-ene-17β-phenylcarbonate, 3β-hydroxy-5α-androst-4-ene-17β-phenylcarbonate, 3-methoxyandrost-4-ene-17β-methylcarbonate, 3β-methoxyandrost-4-ene-17β-methylcarbonate, 3α-methoxyandrost-4-ene-17β-ethylcarbonate, 3β-methoxyandrost-4-ene-17β-ethylcarbonate, 3α-methoxyandrost-4-ene-17β-propylcarbonate, 3β-methoxyandrost-4-ene-17β-propylcarbonate, 3α-methoxyandrost-4-ene-17β-butylcarbonate, 3β-methoxyandrost-4-ene-17β-butylcarbonate, 3α-methoxyandrost-4-ene-17β-hexylcarbonate, 3β-methoxyandrost-4-ene-17β-hexylcarbonate, 3α-methoxyandrost-4-ene-17β-phenylcarbonate, 3β-methoxyandrost-4-ene-17β-phenylcarbonate, 3α-ethoxyandrost-4-ene-17β-methylcarbonate, 3β-ethoxyandrost-4-ene-17β-methylcarbonate, 3α-ethoxyandrost-4-ene-17β-ethylcarbonate, 3β-ethoxyandrost-4-ene-17β-ethylcarbonate, 3α-ethoxyandrost-4-ene-17β-propylcarbonate, 3β-ethoxyandrost-4-ene-17β-propylcarbonate, 3α-ethoxyandrost-4-ene-17β-butylcarbonate, 3β-ethoxyandrost-4-ene-17β-butylcarbonate, 3α-ethoxyandrost-4-ene-17β-hexylcarbonate, 3β-ethoxyandrost-4-ene-17β-hexylcarbonate, 3α-ethoxyandrost-4-ene-17β-phenylcarbonate, 3β-ethoxyandrost-4-ene-17β-phenylcarbonate, 3α-hydroxyandrost-1,4-diene-17β-methylcarbonate, 3β-hydroxyandrost-1,4-diene-17β-methylcarbonate, 3-oxoandrost-1,4-diene-17β-methylcarbonate, 3α-hydroxy-19-norandrost-1,4-diene-17β-methylcarbonate, 3β-hydroxy-19-norandrost-1,4-diene-17β-methylcarbonate, 3-oxo-19-norandrost-1,4-diene-17β-methylcarbonate or an analog of any of these compounds that contains a hydroxyl at the 3-position where the analog is a carbonate, a hydroxyl ester, or a hydroxyl ether where the carbonate, hydroxyl ester or hydroxyl ether is optionally selected from the group consisting of —O—C(O)—O—CH 3 , —O—C(O)—O—C 2 H 5 , —O—C(O)—O—C 4 H 9 , —O—C(O)—CH 3 , —O—C(O)—CF 3 , —O—C(O)—C 2 H 5 , —OCH 3 , —OCH 2 OCH 3 , —OCH 2 SCH 3 , —OC 2 H 5  and —OC 3 H 7 .    
     
     
         17 . The composition of  claim 1  wherein the composition contains 3α-hydroxy-5α-androst-1-ene-17β-methylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-methylcarbonate, 3-oxo-5α-androst-1-ene-17β-methylcarbonate, 3-hydroxy-5α-androst-1-ene-17β-ethylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-ethylcarbonate, 3-oxo-5α-androst-1-ene-17β-ethylcarbonate, 3α-hydroxy-19-nor-5α-androst-1-ene-17β-methylcarbonate, 3β-hydroxy-19-nor-5α-androst-1-ene-17β-methylcarbonate, 3-oxo-19-nor-5α-androst-1-ene-17β-methylcarbonate, 3α-hydroxy-19-nor-5α-androst-1-ene-17β-ethylcarbonate, 3β-hydroxy-19-nor-5α-androst-1-ene-17β-ethylcarbonate or 3-oxo-19-nor-5α-androst-1-ene-17β-ethylcarbonate; and 
 3α-hydroxyandrost-4-ene-17β-methylcarbonate, 3β-hydroxyandrost-4-ene-17β-methylcarbonate, 3α-hydroxyandrost-4-ene-17β-ethylcarbonate or 3β-hydroxyandrost-4-ene-17β-ethylcarbonate.    
     
     
         18 . A method to treat wasting or weight loss in a subject in need thereof comprising administering to the subject, an effective amount of one or two compounds having the structure  
       
         
           
           
               
               
           
         
       
       wherein 
 R 2  is —H, —OH, OR PR , ═O, —SH, SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 3  is —H, —OH, —OR PR , —SH, SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 5  and R 6  independently are —H, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl;  
 R 7  is —CHR 10 —, —CHR 10 —CHR 10 —, —CHR 10 —CHR 10 —CHR 10 —, —CHR 10 —O—CHR 10 —, —CHR 10 —S—CHR 10 —, —CHR 10 —NR PR —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, wherein R 10  independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 8  is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 8  is absent, leaving a 5-membered ring, wherein R 10  independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 9  is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 9  is absent, leaving a 5-membered ring, wherein R 10  independently are —H, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, a thioester, an amide, an amino acid, a peptide, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide, a nucleoside, a nucleotide, an oligonucleotide or a polymer;  
 R PR  independently or together are —H, or protecting groups;  
 R 13  independently are C 1 -C 6  alkyl; and  
 (a) R 1  is —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer; and  
 one R 4  is a carbonate and the other R 4  is —H, —OH, —OR PR , —SH, —SR PR , —N 3 , —NH 2 , —N(R PR ) 2 , —CN, —NO 2 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer; or,  
 (b) R 1  is a carbonate; and  
 R 4  independently are —H, —OH, —OR PR , —SH, —SR PR , —N 3 , —NH 2 , —N(R PR ) 2 , —CN, —NO 2 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer, provided that R 4  are not both —H.  
 
     
     
         19 . The method of  claim 18  wherein 
 (i) 3α-hydroxy-5α-androst-1-ene-17β-methylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-methylcarbonate, 3α-hydroxy-5α-androst-1-ene-17β-ethylcarbonate, 3β-hydroxy-5α-androst-1-ene-17β-ethylcarbonate, 3-oxo-5α-androst-1-ene-17β-methylcarbonate, 3α-hydroxy-19-nor-5α-androst-1-ene-17β-methylcarbonate, 3β-hydroxy-19-nor-5α-androst-1-ene-17β-methylcarbonate, 3-oxo-19-nor-5α-androst-1-ene-17β-methylcarbonate or an analog of any of these compounds that contains a hydroxyl at the 3-position where the analog is a carbonate, a hydroxyl ester, or a hydroxyl ether where the carbonate, hydroxyl ester or hydroxyl ether is optionally selected from the group consisting of —O—C(O)—O—CH 3 , —O—C(O)—O—C 2 H 5 , —O—C(O)—O—C 4 H 9 , —O—C(O)—CH 3 , —O—C(O)—CF 3 , —O—C(O)—C 2 H 5 , —OCH 3 , —OCH 2 OCH 3 , —OCH 2 SCH 3 , —OC 2 H 5  and —OC 3 H 7  and    (ii) 3α-hydroxyandrost-4-ene-17β-methylcarbonate, 3β-hydroxyandrost-4-ene-17β-methylcarbonate, 3α-hydroxyandrost-4-ene-17β-ethylcarbonate, 3β-hydroxyandrost-4-ene-17β-ethylcarbonate, 3-oxoandrost-4-ene-17β-methylcarbonate, 3α-hydroxy-19-norandrost-4-ene-17β-methylcarbonate, 3β-hydroxy-19-norandrost-4-ene-17β-methylcarbonate, 3-oxo-19-norandrost-4-ene-17β-methylcarbonate, 3α-hydroxyandrost-1,4-diene-17β-methylcarbonate, 3β-hydroxyandrost-1,4-diene-17β-methylcarbonate, 3-oxoandrost-1,4-diene-17β-methylcarbonate, 3α-hydroxy-19-norandrost-1,4-diene-17β-methylcarbonate, 3β-hydroxy-19-norandrost-1,4-diene-17β-methylcarbonate, 3-oxo-19-norandrost-1,4-diene-17β-methylcarbonate or an analog of any of these compounds that contains a hydroxyl at the 3-position where the analog is carbonate, a hydroxyl ester, or a hydroxyl ether where the carbonate, hydroxyl ester or hydroxyl ether is optionally selected from the group consisting of —O—C(O)—O—CH 3 , —O—C(O)—O—C 2 H 5 , —O—C(O)—O—C 4 H 9 , —O—C(O)—CH 3 , —O—C(O)—CF 3 , —O—C(O)—C 2 H 5 , —OCH 3 , —OCH 2 OCH 3 , —OCH 2 SCH 3 , —OC 2 H 5  and —OC 3 H 7 , are administered to the subject.    
     
     
         20 . The method of  claim 19  wherein the subject is a human, a rodent or a primate that has an immune suppression condition, the one or two compounds are administered by an oral, buccal, sublingual or parenteral route and, optionally wherein the the one or two compounds are administered as a formulation comprising one or more excipients selected from the group consisting of water, α-cyclodextrin, β-cyclodextrin, binders, disintegrants and lubricants, or optionally wherein the formulation is a slow or controlled release formulation.  
     
     
         21 . A method to treat a viral infection comprising administering to a subject having the infection an effective amount of an antiviral agent and a compound selected from the group consisting of 3α,17β-dihydroxy-16α-fluoroandrost-5-ene, 3α-hydroxy-16α-fluoro-17-oxoandrost-5-ene, 3α,16α,17β-trihydroxy-5α-androstane, 3β,16α,17β-trihydroxy-5α-androstane, 3β,16α-dihydroxy-17-oxo-5α-androstane and 3α,16α-dihydroxy-17-oxo-5α-androstane.  
     
     
         22 . The method of  claim 21  wherein the subject is a human or a primate, the viral infection is a retroviral infection and the antiviral agent is a reverse transcriptase inhibitor or a protease inhibitor.  
     
     
         23 . A method to treat a subject having an immunosuppression condition or an unwanted immune response, wherein the immunosuppression condition or unwanted immune response are associated with an autoimmune disease and/or an immunosuppressive therapy, comprising administering an effective amount of a compound having the formula  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is —OH, —OR PR , —SH, SR PR , —N(R PR ) 2 , ═NOH, ═NOC(O)CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 2  is —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 3  is —OH, —OR PR , —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 4  independently are —H, —OH, —OR PR , —SH, —SR PR , —N 3 , —NH 2 , —N(R PR ) 2 , —CN, —NO 2 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer, provided that R 4  are not both —H;  
 R 5  and R 6  independently are —H, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl;  
 R 7  is —CHR 10 —, —CHR 10 —CHR 10 —, —CHR 10 —CHR 10 —CHR 10 —, —CHR 10 —O—CHR 10 —, —CHR 10 —S—CHR 10 —, —CHR 10 —NR PR —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR  CHR 10 —, wherein R 10  independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 8  is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 8  is absent, leaving a 5-membered ring, wherein R 10  independently are —H, —OH, —OR PR , ═O, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, an ester, a thioester, a phosphoester, a phosphothioester, a phosphonoester, a phosphiniester, a sulfite ester, a sulfate ester, an amide, an amino acid, a peptide, an ether, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide or a polymer;  
 R 9  is —CHR 10 —, —CHR 10 —CHR 10 —, —O—, —O—CHR 10 —, —S—, —S—CHR 10 —, —NR PR — or —NR PR —CHR 10 —, or R 9  is absent, leaving a 5-membered ring, wherein R 10  independently are —H, —SH, —SR PR , ═S, ═CH 2 , —N 3 , —NH 2 , —N(R PR ) 2 , —O—Si—(R 13 ) 3 , —CN, —NO 2 , ═NOH, ═NOC(O)CH 3 , —C(O)—CH 3 , —F, —Cl, —Br, —I, a thioester, an amide, an amino acid, a peptide, a thioether, an acyl group, a thioacyl group, a carbonate, a carbamate, a thioacetal, optionally substituted alkenyl, optionally substituted alkynyl, an optionally substituted aryl moiety, an optionally substituted heteroaryl moiety, optionally substituted monosaccharide, optionally substituted oligosaccharide, a nucleoside, a nucleotide, an oligonucleotide or a polymer;  
 R PR  independently or together are —H, or protecting groups; and  
 R 13  independently are C 1 -C 6  alkyl.  
 
     
     
         24 . The method of  claim 23  wherein the subject is a human, the autoimmune disease is systemic lupus erythematosus or multiple sclerosis and the compound is 3α,17β-dihydroxy-16α-fluoroandrost-5-ene, 3α-hydroxy-16α-fluoro-17-oxoandrost-5-ene, 3α,16α,17β-trihydroxy-5α-androstane, 3β,16α,17-trihydroxy-5α-androstane, 3β,16α-dihydroxy-17-oxo-5α-androstane or 3α,16α-dihydroxy-17-oxo-5α-androstane.