Hydroxyprogesterone heptanoate

Hydroxyprogesterone heptanoate
Clinical data
Trade names	H.O.P, Hydroxyprogesterone, Lutogil A.P., Lutogyl A.P., others
Other names	OHPH; Hydroxyprogesterone enanthate; OHPE; 17α-Hydroxyprogesterone heptanoate; 17α-Hydroxyprogesterone heptylate; 17α-Hydroxypregn-4-ene-3,20-dione 17α-heptanoate; 17α-Heptyloylpregn-4-ene-3,20-dione
Routes of; administration	Intramuscular injection
Drug class	Progestogen; Progestin; Progestogen ester
ATC code	G03DA03 (WHO) ;
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-Acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] heptanoate;
CAS Number	4596-16-1 ; 1079269-78-5;
PubChem CID	94296;
ChemSpider	85099;
UNII	HGN17RX8K8;
CompTox Dashboard (EPA)	DTXSID70196666 ;
ECHA InfoCard	100.022.724
Chemical and physical data
Formula	C28H42O4
Molar mass	442.640 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C;
	InChI InChI=1S/C28H42O4/c1-5-6-7-8-9-25(31)32-28(19(2)29)17-14-24-22-11-10-20-18-21(30)12-15-26(20,3)23(22)13-16-27(24,28)4/h18,22-24H,5-17H2,1-4H3/t22-,23+,24+,26+,27+,28+/m1/s1; Key:NKJYZYWCGKSMSV-BDPSOKNUSA-N;

Hydroxyprogesterone heptanoate (OHPH), also known as hydroxyprogesterone enanthate (OHPE) and sold under the brand names H.O.P., Lutogil A.P., and Lutogyl A.P. among others, is a progestin medication used for progestogenic indications.^[1]^[2]^[3]^[4] It has been formulated both alone and in together with estrogens, androgens/anabolic steroids, and other progestogens in several combination preparations (brand names Tocogestan, Trioestrine Retard, and Triormon Depositum).^[4]^[5]^[6]^[7]^[8]^[9]^[10] OHPH is given by injection into muscle at regular intervals.^[11]^[9]

OHPH is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[12]^[13]^[14] It appears to have similar pharmacology to that of the closely related medication hydroxyprogesterone caproate (OHPC).^[15]^[16]^[17]

OHPH was first described by 1954^[16] and was introduced for medical use by 1957.^[6] It has been used clinically in France and Monaco in the past but is no longer marketed.^[2]^[3]^[4]

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 665–. ISBN 978-1-4757-2085-3.
^ ^a ^b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 532–. ISBN 978-3-88763-075-1.
^ ^a ^b Muller NF, Dessing RP (19 June 1998). European Drug Index: European Drug Registrations (Fourth ed.). CRC Press. pp. 612–. ISBN 978-3-7692-2114-5.
^ ^a ^b ^c Kleemann A, Engel J (2001). Pharmaceutical Substances: Syntheses, Patents, Applications. Thieme. p. 1033. ISBN 978-3-13-558404-1.
^ Cite error: The named reference SascoGendre1998 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference ErmigliaValli1957 was invoked but never defined (see the help page).
^ Cite error: The named reference Bordier1963 was invoked but never defined (see the help page).
^ Cite error: The named reference ExcerptaMedica1981 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference ScholarlyEditions2013 was invoked but never defined (see the help page).
^ Cite error: The named reference Frigerio1981 was invoked but never defined (see the help page).
^ Cite error: The named reference Krówczyński1987 was invoked but never defined (see the help page).
^ Cite error: The named reference Schindler2014 was invoked but never defined (see the help page).
^ Cite error: The named reference BińkowskaWoroń2015 was invoked but never defined (see the help page).
^ Cite error: The named reference PosaciSmitz2000 was invoked but never defined (see the help page).
^ Cite error: The named reference NeumannElger1969 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Junkmann1954 was invoked but never defined (see the help page).
^ Cite error: The named reference Junkmann1959 was invoked but never defined (see the help page).

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 665–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 532–. ISBN 978-3-88763-075-1.

[Muller1998-3] Muller NF, Dessing RP (19 June 1998). European Drug Index: European Drug Registrations (Fourth ed.). CRC Press. pp. 612–. ISBN 978-3-7692-2114-5.

[KleemannEngel2001-4] Kleemann A, Engel J (2001). Pharmaceutical Substances: Syntheses, Patents, Applications. Thieme. p. 1033. ISBN 978-3-13-558404-1.

[SascoGendre1998-5] Cite error: The named reference SascoGendre1998 was invoked but never defined (see the help page).

[ErmigliaValli1957-6] Cite error: The named reference ErmigliaValli1957 was invoked but never defined (see the help page).

[Bordier1963-7] Cite error: The named reference Bordier1963 was invoked but never defined (see the help page).

[ExcerptaMedica1981-8] Cite error: The named reference ExcerptaMedica1981 was invoked but never defined (see the help page).

[ScholarlyEditions2013-9] Cite error: The named reference ScholarlyEditions2013 was invoked but never defined (see the help page).

[Frigerio1981-10] Cite error: The named reference Frigerio1981 was invoked but never defined (see the help page).

[Krówczyński1987-11] Cite error: The named reference Krówczyński1987 was invoked but never defined (see the help page).

[Schindler2014-12] Cite error: The named reference Schindler2014 was invoked but never defined (see the help page).

[BińkowskaWoroń2015-13] Cite error: The named reference BińkowskaWoroń2015 was invoked but never defined (see the help page).

[PosaciSmitz2000-14] Cite error: The named reference PosaciSmitz2000 was invoked but never defined (see the help page).

[NeumannElger1969-15] Cite error: The named reference NeumannElger1969 was invoked but never defined (see the help page).

[Junkmann1954-16] Cite error: The named reference Junkmann1954 was invoked but never defined (see the help page).

[Junkmann1959-17] Cite error: The named reference Junkmann1959 was invoked but never defined (see the help page).

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