Chlormadinone caproate

Chlormadinone caproate
Clinical data
Other names	CMC; Chlormadinone hexanoate; 6-Chloro-17α-hydroxy-Δ6-progesterone hexanoate; 6-Chloro-17α-hydroxypregna-4,6-diene-3,20-dione hexanoate
Routes of; administration	Intramuscular injection
Drug class	Progestogen; Progestin; Progestogen ester
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-Acetyl-6-chloro-10,13-dimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate;
CAS Number	35753-51-6 ;
UNII	RDK6BG5Q4K;
Chemical and physical data
Formula	C27H37ClO4
Molar mass	461.04 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(C(CCCCC)=O)[C@@](C(C)=O)1CC[C@]([H])2[C@@]([H])3C=C(Cl)C4=CC(CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O;
	InChI InChI=1S/C27H37ClO4/c1-5-6-7-8-24(31)32-27(17(2)29)14-11-21-19-16-23(28)22-15-18(30)9-12-25(22,3)20(19)10-13-26(21,27)4/h15-16,19-21H,5-14H2,1-4H3/t19-,20 ,21 ,25-,26 ,27 /m1/s1; Key:VNEYSFJFVXCAHG-BRWSOWNCSA-N;

Chlormadinone caproate (CMC) is a progestin and a progestogen ester which was studied for potential use in combined injectable contraceptives but was never marketed.^[1]^[2]^[3]^[4] It was assessed in combination with estradiol valerate at doses of 80 mg and 3 mg, respectively.^[1]^[2]^[3] In addition to chlormadinone acetate (CMA), analogues of CMC include gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, megestrol caproate, and methenmadinone caproate.^[5]

References

^ ^a ^b Daniel R. Mishell (1983). Long-acting Steroid Contraception. Raven Press. pp. 69, 77. ISBN 978-0-89004-932-7.
^ ^a ^b Toppozada MK (April 1994). "Existing once-a-month combined injectable contraceptives". Contraception. 49 (4): 293–301. doi:10.1016/0010-7824(94)90029-9. PMID 8013216.
^ ^a ^b Newton JR, D'arcangues C, Hall PE (1994). "A review of "once-a-month" combined injectable contraceptives". J Obstet Gynaecol (Lahore). 4 (Suppl 1): S1–34. doi:10.3109/01443619409027641. PMID 12290848.
^ Bopp RJ, Murphy HW, Nash JF, Novotny CR (September 1972). "GLC determination of chlormadinone acetate in plasma". J Pharm Sci. 61 (9): 1441–4. doi:10.1002/jps.2600610919. PMID 4115914.
^ Bouchard, P. (2005). "Chlormadinone acetate (CMA) in oral contraception--a new opportunity". The European Journal of Contraception & Reproductive Health Care. 10 (Suppl 1): 7–11. doi:10.1080/13625180500434889. ISSN 1362-5187. PMID 16356876. S2CID 22898956.

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Clinical data

Other names	CMC; Chlormadinone hexanoate; 6-Chloro-17α-hydroxy-Δ⁶-progesterone hexanoate; 6-Chloro-17α-hydroxypregna-4,6-diene-3,20-dione hexanoate
Routes of administration	Intramuscular injection
Drug class	Progestogen; Progestin; Progestogen ester
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17R)-17-Acetyl-6-chloro-10,13-dimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
CAS Number	35753-51-6^Y
UNII	RDK6BG5Q4K
Chemical and physical data
Formula	C₂₇H₃₇ClO₄
Molar mass	461.04 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O(C(CCCCC)=O)[C@@](C(C)=O)1CC[C@]([H])2[C@@]([H])3C=C(Cl)C4=CC(CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O
InChI InChI=1S/C27H37ClO4/c1-5-6-7-8-24(31)32-27(17(2)29)14-11-21-19-16-23(28)22-15-18(30)9-12-25(22,3)20(19)10-13-26(21,27)4/h15-16,19-21H,5-14H2,1-4H3/t19-,20 ,21 ,25-,26 ,27 /m1/s1 Key:VNEYSFJFVXCAHG-BRWSOWNCSA-N