Hydroxyprogesterone caproate
-
Hydroxyprogesterone caproate
structure -
-
CAS No:
630-56-8
-
Formula:
C27H40O4
-
Chemical Name:
Hydroxyprogesterone caproate
-
Synonyms:
Pregn-4-ene-3,20-dione,17-[(1-oxohexyl)oxy]-;Pregn-4-ene-3,20-dione,17-hydroxy-,hexanoate;Progesterone,17-hydroxy-,hexanoate;Hexanoic acid,ester with 17-hydroxypregn-4-ene-3,20-dione;17-[(1-Oxohexyl)oxy]pregn-4-ene-3,20-dione;Delalutin;3,20-Dioxopregn-4-en-17α-yl caproate;Hormofort;HPC;17α-Hydroxypregn-4-ene-3,20-dione caproate;17α-Hydroxypregn-4-ene-3,20-dione hexanoate;17α-Hydroxyprogesterone n-caproate;17α-Hydroxyprogesterone caproate;17α-Hydroxyprogesterone hexanoate;Proluton Depot;Syngynon;Hydroxyprogesterone caproate;Hydroxyprogesterone hexanoate;Progesterone caproate;Depo-proluton;17α-Caproyloxypregn-4-ene-3,20-dione;Primolut Depot;Neolutin;Pharlon;Proge;Hyproval PA;Lewntogest;Teralutil;NSC 17592;Procyte Depo;17α-Caproyloxyprogesterone;17α-Caproyloxy-P4;17-Caproxyprogesterone;106111-89-1;2247-38-3;91037-33-1;552314-18-8
-
Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System
-
CAS No:
Description
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under the trade name Delalutin by Squibb, which was approved by the U.S. Food and Drug Administration (FDA) in 1956 and withdrawn from marketing in 1999.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.
Hydroxyprogesterone caproate Basic Attributes
428.60400
428.60
211-138-8
276F2O42F5
17592
DTXSID6043915
C960
2937230000
Characteristics
60.44000
5.96960
White or almost White Crystalline power
1.1 g/cm3
119-121 °C
536.4ºC at 760 mmHg
227.6ºC
1.533
Safety Information
NONH for all modes of transport
3
R61
53-22-36/37/39-45
TU5085000
T
P201-P280-P308 + P313
H360
|Danger|H360 (93.02%): May damage fertility or the unborn child [Danger Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 43 companies from 6 notifications to the ECHA C&L Inventory.
Toxicity
Injection site pain is the most common adverse effect associated with hydroxyprogesterone caproate. Other commonly reported adverse effects include: injection site swelling, urticaria, pruritus, injection site pruritus, nausea, injection site nodule, and diarrhea. (4)
Hydroxyprogesterone caproate is extensively protein bound in the plasma. (3)
Drug Information
Hydroxyprogesterone caproate is indicated for the prevention of spontaneous preterm births in singleton pregnancies in women who have previously had a spontaneous preterm birth. (1)|FDA Label
No specific pharmacodynamic studies have been performed to assess hydroxyprogesterone caproate injections. (4) However, the mechanism of action is likely related to increased interaction between progesterone and progesterone receptors. (5)
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.)
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)
The main enzymes involved in metabolism of hydroxyprogesterone caproate are cytochrome P450 (CYP) 3A4 and to a lesser extent CYP3A5. (3)
Half-life = 16 days (±6 days). (3)
The mechanism by which progesterone prevents preterm birth is not well understood, but many pathways are likely involved. (1) Progesterone plays a vital role in regulation of the female reproductive system and is important for successful implantation of the embryo and maintenance of pregnancy. It acts by binding to progesterone receptors in the uterus, ovaries, breasts and in the central nervous system. These receptors exist in 2 isoforms, PR-A and PR-B. Progesterone binding to these receptors ultimately leads to regulation of gene transcription. (2) This results in an anti-inflammatory effect which blunts the proinflammatory state that occurs with initiation of labor, and maintains uterine queiscence by stabilizing progesterone acting on the myometrium. (2)
17 alpha Hydroxy Progesterone Caproate
Hydroxyprogesterone caproate Use and Manufacturing
Hydroxyprogesterone caproate (OHPC) (INN, USAN, JAN) (brand names Delalutin, Proluton, Makena, Prodrox, Hylutin, many others), also known as hydroxyprogesterone hexanoate (BANM), is a steroidal progestin and derivative of 17α-hydroxyprogesterone (17α-OHP) that is related to other 17α-OHP derivatives such as chlormadinone acetate, cyproterone acetate, medroxyprogesterone acetate, and megestrol acetate. It is an ester of 17α-OHP formed from caproic acid (hexanoic acid).OHPC was previously marketed under the trade name Delalutin by Squibb, which was approved by the United States (U.S.) Food and Drug Administration (FDA) in 1956 and withdrawn from marketing in 1999. It is also sold as Proluton throughout Europe. 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.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Computed Properties
Molecular Weight:428.6
XLogP3:5.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:428.29265975
Monoisotopic Mass:428.29265975
Topological Polar Surface Area:60.4
Heavy Atom Count:31
Complexity:797
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
When used in combination with estradiol valerate, it inhibits ovulation, changes the physical and chemical properties of cervical mucus and its effects on the endometrium, interferes with the synchronization of the development of the endometrium and the fertilized egg, and thus affects the fertilization of the egg and the implantation process of the fertilized egg.
Registered Holders
-
STEROID SPA
Active
United States
-
SYMBIOTEC PHARMALAB PRIVATE LTD
Active
United States
-
Aspen Oss B.V.
Active
Netherlands
Recommended Suppliers of Hydroxyprogesterone caproate
-
![China]()
CN
3 YRS
Business licensedTrader Supplier of Estradiol,Progesterone,GS441524,4-Butylresorcinol,DeoxyArbutin,Coenzyme Q10,Piracetam,Pregabalin,Ketoprofen,omeprazole,Fullerene C60,Melatonin,Nicotinamide riboside chloride,lactoferrin,Tylosin tartrate,Gentamycin Sulfate,Levamisole HCl,Praziquantel,Ivermectin,GA3,Pepsin,MT2,5 amino 1MQ,selank,semaxInquiryCAS No.: 630-56-8Grade: Pharmaceutical GradeContent: 99% -
![China]()
CN
5 YRS
Business licensed Certified factoryManufactory Supplier of Dichloromethane,Linocaine hydrochloride -
![China]()
CN
6 YRS
Business licensed Certified factoryManufactory Supplier of Drospirenone,Tretinoin,Tranexamic acid,Tretinoin,Desogestrel,Diosmin,Isotretinoin,Ambroxol hcl,Brimonidine Tartrate,Bromhexine hcl,Isotretinoin,Dydrogesterone,Sulfacetamide sodium,Minoxidil,Pentosan Polysulfate Sodium,Tosyl chloride,4-Nitrobenzaldehyde,Bakuchiol,D-Chiro Inositol -
![China]()
CN
3 YRS
Business licensedTrader Supplier of api,Intermediates,Organic Chemistry,Inorganic Chemistry,Daily Chemicals,Cosmetic Raw Materals,CATALYST AND AUXILIARY,FLAVORS AND FRAGRANCES,Chemical Pesticides,ADDITIVEInquiryCAS No.: 630-56-8Grade: Analytical ReagentContent: 99% -
![China]()
CN
2 YRS
Business licensedTrader Supplier of ghk cuInquiryCAS No.: 630-56-8Grade: Pesticide GradeContent: 99%
Learn More Other Chemicals
-
B-NAPHTHYL CAPROATE
71974-08-8
-
Calcium caproate
38708-95-1
-
Cholesteryl caproate
1062-96-0
-
Gestonorone caproate Formula
1253-28-7
-
Allyl caproate Formula
123-68-2
-
Testosterone caproate Formula
10312-45-5
-
Orforglipron Structure
2212020-52-3
-
Cevimeline hydrochloride Structure
107220-28-0
-
What is 1-Butanone, 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-, (2E)-2-butenedioate (1:1)
97928-20-6
-
What is Timbetasin acetate
1346423-89-9