Hydroxyprogesterone heptanoate

Last updated
Hydroxyprogesterone heptanoate
Hydroxyprogesterone heptanoate.svg
Clinical data
Trade names H.O.P, Hydroxyprogesterone, Lutogil A.P., Lutogyl A.P., others
Other namesOHPH; 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
Identifiers
  • [(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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.022.724 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C28H42O4
Molar mass 442.640 g·mol−1
3D model (JSmol)
  • CCCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C
  • 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]

Contents

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]

Medical uses

OHPH is a progestogen and was used in situations in which progestogens were indicated. [12] [13] [14]

Available forms

OHPH was provided as a 125 mg/1 mL oil solution for use by intramuscular injection. [3] [11] In addition to single-drug preparations, OHPH has also been used in a number of multi-drug formulations. [4] [5] [6] [7] [8] [9] [10] It was used in Tocogestan, a combination of 50 mg progesterone, 200 mg OHPH, and 250 mg α-tocopherol palmitate (vitamin E) in oil solution for use by intramuscular injection. [18] [4] [5] It was also used in Triormon Depositum (estradiol dibutyrate, testosterone caproate, and OHPH) and Trioestrine Retard (estradiol diundecylate, testosterone cyclohexylpropionate, and OHPH). [6] [7] OHPH was a component of the experimental preparation Trophobolene (or Trophoboline), which also contained estrapronicate (estradiol nicotinate propionate) and nandrolone undecanoate, as well. [8] [9] [10]

Pharmacology

Pharmacodynamics

OHPH is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. [15] [12] [13] [14] The progestogenic potency of OHPH in the uterus is equal to or greater than that of progesterone when administered by subcutaneous injection in animals. [15] [16] [17] Its potency in animals likewise appears to be similar to that of hydroxyprogesterone caproate. [15] [16] [17]

Pharmacokinetics

OHPH shows a pronounced depot effect when administered by subcutaneous injection in animals, similarly to the closely related medication hydroxyprogesterone caproate. [15] [16] The oral activity of OHPH in animals does not appear to have been assessed. [15]

Chemistry

OHPH, also known as hydroxyprogesterone enanthate (OHPE), [19] as well as 17α-hydroxyprogesterone heptanoate or 17α-hydroxypregn-4-ene-3,20-dione 17α-heptanoate, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone. [1] [2] It is a progestogen ester; specifically, it is the C17α heptanoate (enanthate) ester of 17α-hydroxyprogesterone. [1] [2] Analogues of OHPH include the more well-known medications hydroxyprogesterone acetate and hydroxyprogesterone caproate (hydroxyprogesterone hexanoate). [1] [2] The C3 benzilic acid hydrazone of OHPH, hydroxyprogesterone heptanoate benzilic acid hydrazone (OHPHBH), is known and has been studied in animals. [20] [21] In terms of chemical structure, OHPH is very similar to hydroxyprogesterone caproate, differing from it only in having one additional carbon in its fatty acid ester chain. [1] [2]

History

OHPH was first described, along with hydroxyprogesterone caproate and hydroxyprogesterone acetate, by Karl Junkmann of Schering AG in 1954. [16] [19] It was introduced for medical use by 1957. [6] OHPH was commercialized by Roussel and Théramex, and has been used clinically in France and Monaco but is no longer marketed. [2] [3] [4]

Society and culture

Brand names

OHPH has been marketed alone under a number of brand names including H.O.P, Hydroxyprogesterone, Lutogil A.P., and Lutogyl A.P. [1] [2] [3] [4]

Availability

OHPH was previously marketed in France and Monaco but is no longer available. [2] [3] [22]

See also

Related Research Articles

Norethisterone acetate

Norethisterone acetate (NETA), also known as norethindrone acetate and sold under the brand name Primolut-Nor among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication available in low-dose and high-dose formulations and is used alone or in combination with an estrogen. It is ingested orally.

Gestonorone caproate

Gestonorone caproate, also known as gestronol hexanoate or norhydroxyprogesterone caproate and sold under the brand names Depostat and Primostat, is a progestin medication which is used in the treatment of enlarged prostate and cancer of the endometrium. It is given by injection into muscle typically once a week.

Ethisterone

Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.

Hydroxyprogesterone caproate

Hydroxyprogesterone caproate (OHPC), sold under the brand names Proluton and Makena among others, is a progestin medication which is used to prevent preterm birth in pregnant women with a history of the condition and to treat gynecological disorders. It has also been formulated in combination with estrogens for various indications and as a form of long-lasting injectable birth control. It is not used by mouth and is instead given by injection into muscle or fat, typically once per week to once per month depending on the indication.

Combined injectable contraceptives (CICs) are a form of hormonal birth control for women. They consist of monthly injections of combined formulations containing an estrogen and a progestin to prevent pregnancy.

Algestone acetophenide

Algestone acetophenide, also known more commonly as dihydroxyprogesterone acetophenide (DHPA) and sold under the brand names Perlutal and Topasel among others, is a progestin medication which is used in combination with an estrogen as a form of long-lasting injectable birth control. It has also been used alone, but is no longer available as a standalone medication. DHPA is not active by mouth and is given once a month by injection into muscle.

Norethisterone enanthate

Norethisterone enanthate (NETE), also known as norethindrone enanthate, is a form of hormonal birth control which is used to prevent pregnancy in women. It is used both as a form of progestogen-only injectable birth control and in combined injectable birth control formulations. It may be used following childbirth, miscarriage, or abortion. The failure rate per year in preventing pregnancy for the progestogen-only formulation is 2 per 100 women. Each dose of this form lasts two months with only up to two doses typically recommended.

Hydroxyprogesterone acetate

Hydroxyprogesterone acetate (OHPA), sold under the brand name Prodox, is an orally active progestin related to hydroxyprogesterone caproate (OHPC) which has been used in clinical and veterinary medicine. It has reportedly also been used in birth control pills.

Estradiol dienantate

Estradiol dienanthate (EDE), sold under the brand names Climacteron among others, is a long-acting estrogen medication which was previously used in menopausal hormone therapy for women and to suppress lactation in women. It was formulated in combination with estradiol benzoate (EB), a short-acting estrogen, and testosterone enanthate benzilic acid hydrazone (TEBH), a long-acting androgen/anabolic steroid. EDE has not been made available for medical use alone. The medication, in combination with EB and TEBH, was given by injection into muscle once or at regular intervals, for instance once every 6 weeks.

Progestogen ester

A progestogen ester is an ester of a progestogen or progestin. The prototypical progestogen is progesterone, an endogenous sex hormone. Esterification is frequently employed to improve the pharmacokinetics of steroids, including oral bioavailability, lipophilicity, and elimination half-life. In addition, with intramuscular injection, steroid esters are often absorbed more slowly into the body, allowing for less frequent administration. Many steroid esters function as prodrugs.

Estradiol benzoate/progesterone Drug combination

Estradiol benzoate/progesterone (EB/P4), sold under the brand names Duogynon and Sistocyclin among others, is a combination medication of estradiol benzoate (EB), an estrogen, and progesterone (P4), a progestogen. It has been formulated both as short-acting oil solutions and long-acting microcrystalline aqueous suspensions and is given by injection into muscle either once or continuously at regular intervals.

Estradiol dibutyrate

Estradiol dibutyrate (EDBu), or estradiol dibutanoate, is an estrogen medication and an estrogen ester – specifically, a diester of estradiol – which is no longer used. It was a component of Triormon Depositum, a combination formulation of estradiol dibutyrate, testosterone caproate, and hydroxyprogesterone heptanoate which was developed in the 1950s.

Methenmadinone caproate

Methenmadinone caproate is a progestin medication which was developed in Czechoslovakia in the 1960s and was studied for potential use in combined injectable contraceptives in the 1970s but was never marketed. It was studied as a combined injectable contraceptive in combination with estradiol valerate at doses of 60 mg and 10 mg, respectively, once a month by intramuscular injection. MMC is the C17α caproate (hexanoate) ester of methenmadinone and an analogue of methenmadinone acetate. In addition to MMA, analogues of MMC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and megestrol caproate.

Estradiol benzoate/estradiol valerate/hydroxyprogesterone caproate (EB/EV/OHPC), sold under the brand name Sin-Ol, is a combination medication of estradiol benzoate (EB), an estrogen, estradiol valerate (EV), an estrogen, and hydroxyprogesterone caproate (OHPC), a progestin, which was reportedly used as a combined injectable contraceptive in women in the early 1970s. It contained 1 mg EB, 10 mg EV, and 250 mg OHPC in oil solution, was provided in the form of 3 mL ampoules, and was administered by intramuscular injection at regular intervals. The medication was manufactured by the pharmaceutical company Reuffer in Mexico.

Estradiol diundecylate/hydroxyprogesterone heptanoate/testosterone cyclohexylpropionate (EDU/OHPH/TCHP), sold under the brand name Trioestrine Retard, is an injectable combination medication of estradiol diundecylate (EDU), an estrogen, hydroxyprogesterone heptanoate (OHPH), a progestogen, and testosterone cyclohexylpropionate (TCHP), an androgen/anabolic steroid. It contained 2.25 mg EDU, 100 mg OHPH, and 67.5 mg TCHP in oil solution, was provided as ampoules, and was administered by intramuscular injection. The medication was manufactured by Roussel and Théramex and was marketed by 1953. It is no longer available.

Estradiol dibutyrate/hydroxyprogesterone heptanoate/testosterone caproate (EDBu/OHPH/TCa), sold under the brand name Triormon Depositum, is an injectable combination medication of estradiol dibutyrate (EDBu), an estrogen, hydroxyprogesterone heptanoate (OHPH), a progestogen, and testosterone caproate (TCa), an androgen/anabolic steroid, which was used in the treatment of menopausal symptoms in women. It contained 3 mg EDBu, 30 mg OHPH, and 50 mg TCa in oil solution and was administered by intramuscular injection. The medication was developed by 1957. It is no longer available.

Estrapronicate/hydroxyprogesterone heptanoate/nandrolone undecanoate (EPC/OHPH/NU), tentative brand name Trophobolene or Trophoboline, is an injectable combination medication of estrapronicate, an estrogen, hydroxyprogesterone heptanoate (OHPH), a progestogen, and nandrolone undecanoate (NU), an androgen/anabolic steroid, which was never marketed. It contained 1.3 mg EPC, 80 mg OHPH, and 50 mg NU in oil solution and was administered by intramuscular injection. The medication was developed by Théramex in the mid-to-late 1960s. It was studied for use for a variety of indications, including treatment of coronary insufficiency, growth deficiency, and osteoporosis, as well as hormonal disorders in gonadotropin deficiency.

Hydroxyprogesterone heptanoate benzilic acid hydrazone

Hydroxyprogesterone heptanoate benzilic acid hydrazone (OHPHBH), also known as 17α-hydroxyprogesterone 17α-heptanoate 3-benzilic acid hydrazone, is a progestin medication which was never marketed. It is the C3 benzilic acid hydrazone of hydroxyprogesterone heptanoate (OHPH). The medication has a longer duration of action than OHPH when administered by subcutaneous injection in animals.

References

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  18. ↑ "Formulation".
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  22. ↑ https://www.micromedexsolutions.com/


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