From Wikipedia, the free encyclopedia
Levonorgestrel cyclopropylcarboxylate Other names HRP-003; HRP003; Levonorgestrel cyclopropyl-carboxylate; Levonorgestrel 17β-cyclopropylcarboxylate; 17α-Ethynyl-18-methyl-19-nortestosterone 17β-cyclopropylcarboxylate; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 17β-cyclopropylcarboxylate; 13-Ethyl-17α-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one cyclopropanecarboxylate Routes of administration Intramuscular injection Drug class Progestogen ; Progestin ; Progestogen ester
[(8R ,9S ,10R ,13S ,14S ,17R )-13-Ethyl-17-ethynyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a ]phenanthren-17-yl] cyclopropanecarboxylate
CAS Number PubChem CID ChemSpider Formula C 25 H 32 O 3 Molar mass 380.528 g·mol−1 3D model (JSmol )
CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OC(=O)C4CC4)CCC5=CC(=O)CC[C@H]35
InChI=1S/C25H32O3/c1-3-24-13-11-20-19-10-8-18(26)15-17(19)7-9-21(20)22(24)12-14-25(24,4-2)28-23(27)16-5-6-16/h2,15-16,19-22H,3,5-14H2,1H3/t19-,20+,21+,22-,24-,25-/m0/s1
Key:TZZXNSUFTUXHRE-AYEDEZQKSA-N
Levonorgestrel cyclopropylcarboxylate (developmental code name HRP-003 ), or levonorgestrel 17β-cyclopropylcarboxylate , is a progestin and a progestogen ester which was studied for potential use as an injectable hormonal contraceptive but was never marketed.[1] [2] [3] [4] [5] [6] [7] [8] [9] [10] It was developed by the World Health Organization 's Special Programme on Human Reproduction in the 1980s.[1] [2] [9] Analogues of levonorgestrel cyclopropylcarboxylate include levonorgestrel cyclobutylcarboxylate (HRP-001) and levonorgestrel butanoate (HRP-002).[1] [2] [3]
See also [ ]
References [ ]
^ a b c Benagiano, G., & Merialdi, M. (2011). Carl Djerassi and the World Health Organisation special programme of research in human reproduction. Journal für Reproduktionsmedizin und Endokrinologie-Journal of Reproductive Medicine and Endocrinology, 8(1), 10-13. http://www.kup.at/kup/pdf/10163.pdf
^ a b c Garza-Flores J, Hall PE, Perez-Palacios G (1991). "Long-acting hormonal contraceptives for women". J. Steroid Biochem. Mol. Biol . 40 (4–6): 697–704. doi :10.1016/0960-0760(91)90293-E . PMID 1958567 . S2CID 26021562 .
^ a b Wu L, Janagam DR, Mandrell TD, Johnson JR, Lowe TL (July 2015). "Long-acting injectable hormonal dosage forms for contraception". Pharm. Res . 32 (7): 2180–91. doi :10.1007/s11095-015-1686-2 . PMID 25899076 . S2CID 12856674 .
^ Runnebaum, B.; Rabe, T.; Kiesel, L. (1988). "Trends in Hormonal Contraception". Female Contraception . pp. 109–121. doi :10.1007/978-3-642-73790-9_9 . ISBN 978-3-642-73792-3 .
^ Marcus Filshie; John Guillebaud (22 October 2013). Contraception: Science and Practice . Elsevier Science. pp. 112–. ISBN 978-1-4831-6366-6 .
^ Elizabeth Connell (4 December 2001). The Contraception Sourcebook . McGraw Hill Professional. p. 133. ISBN 978-0-07-139945-6 .
^ Gerald I. Zatuchni; Northwestern University (Evanston, Ill.). Program for Applied Research on Fertility Regulation (1984). Long-Acting Contraceptive Delivery Systems: Proceedings of an International Workshop on Long-Acting Contraceptive Delivery Systems, May 31-June 3, 1983, New Orleans, Louisiana . Harper & Row Pub. p. 196. ISBN 978-0-06-142905-7 .
^ Egon Diczfalusy (1987). Fertility regulation today and tomorrow . Raven Press. p. 132. ISBN 978-0-88167-180-3 .
^ a b Seiichi Matsumoto; Japan Family Planning Association (1987). Recent advances in fertility control: proceedings of the 1st International Symposium on Recent Advances in Fertility Control, Tokyo, November 8, 1986 . Excerpta Medica. p. 67. ISBN 978-90-219-1638-5 .
^ L. R. Sitruk-Ware; C. Wayne Bardin (1992). Contraception: newer pharmacological agents, devices, and delivery systems . M. Dekker. p. 62. ISBN 978-0-8247-8700-4 .
AR
Agonists
Testosterone derivatives: 4-Androstenediol
4-Dehydroepiandrosterone (4-DHEA)
4-Hydroxytestosterone
5-Androstenedione
11-Ketotestosterone
11β-Hydroxyandrostenedione
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
Androstenediol (5-androstenediol)
Androstenedione (4-androstenedione)
Atamestane
Boldenone
Boldione (1,4-androstadienedione)
Clostebol
Clostebol acetate
Clostebol caproate
Clostebol propionate
Cloxotestosterone
Cloxotestosterone acetate
Dehydroandrosterone
DHEA (androstenolone, prasterone; 5-DHEA)
DHEA enanthate (prasterone enanthate)
DHEA sulfate
Exemestane
Formestane
Plomestane
Quinbolone
Silandrone
Testosterone # (+dutasteride )
17α-Ethynyl-19-nortestosterone derivatives: Δ4 -Tibolone
Desogestrel
Etonogestrel
Etynodiol
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Norethisterone
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Norgestrel
Norgestrienone
Quingestanol
Tibolone
Mixed (SARMs )
Steroidal:
MK-0773
TFM-4AS-1
YK-11
Antagonists
Nonsteroidal: 5N -Bicalutamide
AA560
Apalutamide
Atraric acid
Bakuchiol
Bicalutamide
Bisphenols (e.g., BADGE , , bisphenol A , bisphenol F , bisphenol S )
BMS-641988
Cimetidine
Cioteronel
Cyanonilutamide
Darolutamide
DDT (via metabolite p,p’-DDE )
Dieldrin
DIMP
Endosulfan
Enzalutamide
EPI-001
EPI-7386
Fenarimol
Flutamide
Hydroxyflutamide
Inocoterone
Inocoterone acetate
Ketoconazole
Ketodarolutamide
Lavender oil
LG-120907
Linuron
Methiocarb
N -Desmethylapalutamide
N -Desmethylenzalutamide
Nilutamide
Pentomone
Phenothrin
Prochloraz
Procymidone
Proxalutamide
Ralaniten (EPI-002)
Ralaniten acetate (EPI-506)
RD-162
Rezvilutamide
RU-22930
RU-56187
RU-57073
RU-58642
RU-58841
Seviteronel
Thalidomide
Topilutamide (fluridil)
Valproic acid
Vinclozolin
GPRC6A
Agonists
Cations (incl. aluminum , calcium , gadolinium , magnesium , strontium , zinc )
Dehydroandrosterone
Dihydrotestosterone
Estradiol
L -α-Amino acids (incl. L -arginine , L -lysine , L -ornithine )
Osteocalcin
SHBG
Testosterone
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids
PR
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Spirolactone derivatives: Canrenoic acid
Canrenone
Drospirenone
Mespirenone
Potassium canrenoate
Prorenone
SC-5233 (spirolactone)
SC-8109
Spironolactone
Spirorenone
Mixed (SPRMs )
Nonsteroidal: Apigenin
Kaempferol
Naringenin
Syringic acid
Antagonists
Nonsteroidal: Darolutamide
Valproic acid
mPR (PAQR )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
Categories :
Abandoned drugs Alkyne derivatives Androgens and anabolic steroids Carboxylic acids Estranes Enones Prodrugs Progestogens Progestogen esters World Health Organization Steroid stubs Genito-urinary system drug stubs Hidden categories:
Articles without EBI source Chemical pages without DrugBank identifier Articles without KEGG source Articles without UNII source Drugs missing an ATC code Drugs with no legal status Articles containing unverified chemical infoboxes All stub articles