Chemistry:MK-434

MK-434
Clinical data
Other names	MK-0434; 17β-Benzoyl-4-aza-5α-androst-1-en-3-one
Routes of; administration	By mouth
Drug class	5α-Reductase inhibitor
Identifiers
	IUPAC name (1S,3aS,3bS,5aR,9aR,9bS,11aS)-1-Benzoyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinolin-7-one;
CAS Number	134067-56-4;
PubChem CID	131705;
ChemSpider	116366;
UNII	J5DR1P0IKK;
Chemical and physical data
Formula	C25H31NO2
Molar mass	377.528 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)C4=CC=CC=C4)CC[C@@H]5[C@@]3(C=CC(=O)N5)C;
	InChI InChI=1S/C25H31NO2/c1-24-14-12-19-17(8-11-21-25(19,2)15-13-22(27)26-21)18(24)9-10-20(24)23(28)16-6-4-3-5-7-16/h3-7,13,15,17-21H,8-12,14H2,1-2H3,(H,26,27)/t17-,18-,19-,20+,21+,24-,25+/m0/s1; Key:ZYTQEOWFSVTRLX-QKONGSNMSA-N;

Short description: Chemical compound

MK-434 is a 5α-reductase inhibitor which was under development in the 1990s by Merck & Co for the treatment of a variety of androgen-dependent conditions including benign prostatic hyperplasia, prostate cancer, pattern hair loss, excessive hair growth, acne, and seborrhea but was never marketed.^[1]^[3]^[2] It acts as a selective inhibitor of 5α-reductase type 2.^[2]^[3]^[4] The drug has been found to decrease circulating dihydrotestosterone levels by a maximum of approximately 50% in men.^[2]^[3] MK-434 is a synthetic 4-azasteroid and is structurally related to other 5α-reductase inhibitors like finasteride.^[3]

References

↑ ^1.0 ^1.1 "MK 434 - AdisInsight". https://adisinsight.springer.com/drugs/800005411.
↑ ^2.0 ^2.1 ^2.2 ^2.3 "Plasma concentrations and effect on testosterone metabolism after single doses of MK-0434, a steroid 5 alpha-reductase inhibitor, in healthy subjects". Eur. J. Clin. Pharmacol. 46 (2): 123–6. 1994. doi:10.1007/bf00199874. PMID 8039530.
↑ ^3.0 ^3.1 ^3.2 ^3.3 "The 5 alpha-reductase system and its inhibitors. Recent development and its perspective in treating androgen-dependent skin disorders". Dermatology (Basel) 193 (3): 177–84. 1996. doi:10.1159/000246242. PMID 8944337.
↑ "The effects of progesterone, 4,16-androstadien-3-one and MK-434 on the kinetics of pig testis microsomal testosterone-4-ene-5alpha-reductase activity". J. Steroid Biochem. Mol. Biol. 60 (5–6): 353–9. March 1997. doi:10.1016/s0960-0760(96)00223-3. PMID 9219928.

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Clinical data

Other names	MK-0434; 17β-Benzoyl-4-aza-5α-androst-1-en-3-one
Routes of administration	By mouth^[1]^[2]
Drug class	5α-Reductase inhibitor
Identifiers
IUPAC name (1S,3aS,3bS,5aR,9aR,9bS,11aS)-1-Benzoyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinolin-7-one
CAS Number	134067-56-4
PubChem CID	131705
ChemSpider	116366
UNII	J5DR1P0IKK
Chemical and physical data
Formula	C₂₅H₃₁NO₂
Molar mass	377.528 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)C4=CC=CC=C4)CC[C@@H]5[C@@]3(C=CC(=O)N5)C
InChI InChI=1S/C25H31NO2/c1-24-14-12-19-17(8-11-21-25(19,2)15-13-22(27)26-21)18(24)9-10-20(24)23(28)16-6-4-3-5-7-16/h3-7,13,15,17-21H,8-12,14H2,1-2H3,(H,26,27)/t17-,18-,19-,20+,21+,24-,25+/m0/s1 Key:ZYTQEOWFSVTRLX-QKONGSNMSA-N