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Home> Encyclopedia >Pharmaceutical>Pharmaceutical Intermediates>Hormones and synthetic substitutes
17a-Hydroxyprogesterone caproate structure
17a-Hydroxyprogesterone caproate structure

17a-Hydroxyprogesterone caproate

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] hexanoate
CAS No.: 630-56-8
Molecular Weight:428.60400
Modify Date.: 2023-02-18 05:04

Hydroxyprogesterone caproate is a synthetic, steroidal progestin; an ester derivative of 17α-hydroxyprogesterone formed from caproic acid.

Hydroxyprogesterone caproate is a corticosteroid hormone.|Hydroxyprogesterone caproate is a synthetic steroid hormone that is similar to medroxyprogesterone acetate and megestrol acetate. It is an ester derivative of 17α-hydroxyprogesterone formed from caproic acid (hexanoic acid). Hydroxyprogesterone caproate was previously marketed under the trade name Delalutin by Squibb, which was approved by the U.S. Food and Drug Administration (FDA) in 1956 and withdrawn from marketing in 1999. The U.S. FDA approved Makena from KV Pharmaceutical (previously named as Gestiva) on February 4, 2011 for prevention of preterm delivery in women with a history of preterm delivery, sparking a pricing controversy.|Hydroxyprogesterone Caproate is a synthetic progestational agent similar to the endogenous progesterone used in hormone therapy or as a female contraceptive. Mimicking the action of progesterone, hydroxyprogesterone caporate binds to and activates nuclear progesterone receptors in the reproductive system and causes the ligand-receptor complex to be translocated to the nucleus where it binds to and promotes expression of target genes. Due to the negative feedback mechanism seen with progesterone, this agent also blocks luteinizing hormone (LH) release from the pituitary gland, thereby leading to an inhibition of ovulation and an alteration in the cervical mucus and endometrium. Furthermore, without stimulation of LH, estrogen release from the ovaries is stopped, hence impeding the growth of estrogen-sensitive tumor cells.|Hydroxyprogesterone derivative that acts as a PROGESTIN and is used to reduce the risk of recurrent MISCARRIAGE and of PREMATURE BIRTH. It is also used in combination with ESTROGEN in the management of MENSTRUATION DISORDERS.

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1. Names and Identifiers
1.1 Name
17a-Hydroxyprogesterone caproate
1.2 Synonyms

(17α)-3,20-Dioxopregn-4-en-17-yl hexanoate (8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl hexanoate (8R,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl hexanoate [(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] hexanoate 17-((1-Oxohexyl)oxy)pregn-4-ene-3,20-dione 17-[(1-Oxohexyl)oxy]pregn-4-ene-3,20-dione 17a-Hydroxyprogesterone Hexanoate 17-Hydroxypregn-4-ene-3,20-dione hexanoate 17α-Caproyloxypregn-4-ene-3,20-dione 17-α-Hexanoyloxypregn-4-ene-3,20-dione 17-α-Hydroxyprogesterone caproate 17-α-hydroxy-progesterone caproate 17α-Hydroxyprogesterone caproate 17-α-Hydroxyprogesterone hexanoate 17α-Hydroxyprogesterone hexanoate 17α-Hydroxyprogesterone n-caproate 3,20-Dioxo-4-pregnen-17α-yl hexanoat 3,20-Dioxopregn-4-en-17-yl hexanoate 3,20-Dioxopregn-4-en-17-ylhexanoat 3,20-Dioxopregn-4-en-17α-yl caproate 3,20-Dioxopregn-4-en-1-yl hexanoate Delalutin EINECS 211-138-8 Gesterol LA 250 Hexanoic acid, (17α)-3,20-dioxopregn-4-en-17-yl ester Hexanoic acid, 3,20-dioxopregn-4-en-17-yl ester Hexanoic acid, 3,20-dioxopregn-4-en-1-yl ester Hexanoic acid, ester with 17-hydroxypregn-4-ene-3,20-dione (8CI) hydroxyprogesterone caproate HYDROXYPROGESTERONECAPROATE,USP MFCD00072134 Pharlon PREGN-4-ENE-3,20-DIONE HEXANOATE Pregn-4-ene-3,20-dione, 17-((1-oxohexyl)oxy)- Pregn-4-ene-3,20-dione, 17-[(1-oxohexyl)oxy]- Pregn-4-ene-3,20-dione, 17-hydroxy-, hexanoate Pregn-4-ene-3,20-dione, 17-hydroxy-, hexanoate (7CI, 8CI) Proge Progesterone, 17-hydroxy-, hexanoate Proluton depot Teralutil

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C27H40O4 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
1.1 g/cm3
2.1 Melting point
2.1 Boiling point
536.4ºC at 760 mmHg
2.1 Refractive index
2.1 Flash Point
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Appearance
White or almost White Crystalline power
3. Use and Manufacturing
3.1 Usage
4. Safety and Handling
4.1 Symbol
4.1 Hazard Codes
4.1 Signal Word
4.1 Risk Statements
4.1 Safety Statements
4.1 Hazard Declaration
NONH for all modes of transport
4.1 Caution Statement
P201-P280-P308 + P313
4.1 WGK Germany
4.1 Toxicity
Drug; Food Toxin; Synthetic Compound

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H360 May damage fertility or the unborn child

Precautionary statement(s)

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.


P308+P313 IF exposed or concerned: Get medical advice/ attention.


P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


7. Other Information
7.0 Mesh
Compounds that interact with PROGESTERONE RECEPTORS in target tissues to bring about the effects similar to those of PROGESTERONE. Primary actions of progestins, including natural and synthetic steroids, are on the UTERUS and the MAMMARY GLAND in preparation for and in maintenance of PREGNANCY. (See all compounds classified as Progestins.)|Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)
7.1 Absorption
Absorption of 17-hydroxyprogesteron caproate is slow, occurring over a long period of time. (3)|Following intramuscular injection, approximately 50% of hydroxyprogesterone caproate metabolites are eliminated in the feces, while approximately 30% of metabolites are eliminated in the urine. (3)|Hydroxyprogesterone caproate has a high volume of distribution. (3)|Clearance is highly variable from patient to patient. (3)
7.2 Metabolism
The main enzymes involved in metabolism of hydroxyprogesterone caproate are cytochrome P450 (CYP) 3A4 and to a lesser extent CYP3A5. (3)
7.3 Biological Half Life
Half-life = 16 days (±6 days). (3)
7.4 Mesh Entry Terms
17 alpha Hydroxy Progesterone Caproate
7.5 Use Classification
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
8. Computational chemical data
  • Molecular Weight: 428.60400g/mol
  • Molecular Formula: C27H40O4
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 428.29265975
  • Monoisotopic Mass: 428.29265975
  • Complexity: 797
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 60.4
  • Heavy Atom Count: 31
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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