ALTRENOGEST

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H26O2
Molecular Weight	310.4299
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)C=CC3=C4CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=VWAUPFMBXBWEQY-ANULTFPQSA-N

InChI=1S/C21H26O2/c1-3-10-21(23)12-9-19-18-6-4-14-13-15(22)5-7-16(14)17(18)8-11-20(19,21)2/h3,8,11,13,18-19,23H,1,4-7,9-10,12H2,2H3/t18-,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4b096dd1-fc17-4db6-8e6d-33413de821e5
Curator's Comment: description was created based on several sources, including etd.lsu.edu/docs/available/etd-08252004-155118/unrestricted/Ferguson_dis.pdf

Altrenogest (INN, USAN, BAN) (brand name Regumate), also known as allyltrenbolone, is a steroidal progestin that is widely used in veterinary medicine to suppress estrus in animals. Altrenogest is an orally active progestin developed for use in the horse. Altrenogest has been chemically modified by addition of a hydroxyl group and 3 carbon chain placed on carbon 17 of the progestin. Research has demonstrated that Altrenogest has low anabolic activity and is 20 times less potent than testosterone or similar progestins when compared for effects on muscle growth in castrated rats

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Synchronization of estrus 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4b096dd1-fc17-4db6-8e6d-33413de821e5	Preventive		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of P.G. 600 on the onset of estrus and ovulation rate in gilts treated with Regu-mate.	2001 Nov	11768102
Effects of ovariohysterectomy on prostaglandin F2alpha-induced nesting behaviour in pigs.	2001 Sep 1-15	11564463
Ovarian response, embryo recovery and results of embryo transfer in a Hungarian native pig breed.	2001 Sep 15	11665896
Quantitative and qualitative assessment of milk production after pharmaceutical induction of lactation in the mare.	2002 Jul-Aug	12141311
Hysteroscopic insemination of mares with low numbers of nonsorted or flow sorted spermatozoa.	2002 Mar	11905434
Hysteroscopic insemination of low numbers of flow sorted fresh and frozen/thawed stallion spermatozoa.	2002 Mar	11902755
Induction of maternal behavior in non-parturient adoptive mares.	2002 Sep	12213513
Ovarian hematoma in an 11-year-old Thoroughbred-Hanovarian mare.	2003 Jul	12892291
The effect of exogenous estradiol benzoate and altrenogest on uterine and ovarian blood flow during the estrous cycle in mares.	2004 Apr 15	15037001
Reproductive physiology and development of artificial insemination technology in killer whales (Orcinus orca).	2004 Aug	15115725
Deslorelin on Day 8 or 12 postovulation does not luteinize follicles during an artificially maintained diestrous phase in the mare.	2004 Jul	15159101
Mitochondrial aggregation patterns and activity in porcine oocytes and apoptosis in surrounding cumulus cells depends on the stage of pre-ovulatory maturation.	2004 Jun	15019463
Effects of a synthetic progestogen, altrenogest, on oestrus synchronisation and fertility in miniature pigs.	2004 Nov 13	15573786
Early-weaned sows: altrenogest therapy, estrus, ovulation, and reproductive performance.	2004 Sep	15302382
Effect of prolonged use of altrenogest on behaviour in mares.	2005 Jan	15683772
Effect of P.G. 600 on the timing of ovulation in gilts treated with altrenogest.	2005 Jul	15956478
Effect of prolonged use of altrenogest on behaviour in mares.	2005 May	15912604
Estrous cycle characterisation and artificial insemination using frozen-thawed spermatozoa in the bottlenose dolphin (Tursiops truncatus).	2005 May	15855629
Management of hydrops amnion in a mare resulting in birth of a live foal.	2006 Apr 15	16618227
Detection of altrenogest and its metabolites in post administration horse urine using liquid chromatography tandem mass spectrometry--increased sensitivity by chemical derivatisation of the glucuronic acid conjugate.	2006 Apr 3	16520102
A preliminary study on the induction of dioestrous ovulation in the mare--a possible method for inducing prolonged luteal phase.	2006 Jul 26	16987391
The use of altrenogest to control aggression in a male Grant's Zebra (Equus burchelli boehmi).	2006 Mar	17312816
Withdrawal period for Regumate Porcine.	2006 Sep 2	16950895
Pharmacokinetics of altrenogest in horses.	2007 Feb	17217407
Luteinizing hormone release after administration of the gonadotropin-releasing hormone agonist Fertilan (goserelin) for synchronization of ovulation in pigs.	2007 Jan	17179548
Synchronization of estrus and ovulation in sows not conceiving in a scheduled fixed-time insemination program.	2007 Jan	16481132
Follicle development during luteal phase and altrenogest treatment in pigs.	2007 Jun	17506814
Responses to delayed estrus after weaning in sows using oral progestagen treatment.	2008 Aug	18407977
Stress and its influence on reproduction in pigs: a review.	2008 Dec 10	19077201
Study on the oestrous synchronization in gilts by using progestin altrenogest and hCG: its effect on the follicular development, ovulation time and subsequent reproductive performance.	2008 Feb	18069947
Effects of altrenogest treatment of mares in late pregnancy on parturition and on neonatal viability of their foals.	2008 Jul	18484066
Ascending placentitis in the mare: A review.	2008 May 1	21851713
Synchronization of ovulation in cyclic gilts with porcine luteinizing hormone (pLH) and its effects on reproductive function.	2008 Oct 15	18656251
Post-weaning altrenogest treatment in primiparous sows; the effect of duration and dosage on follicular development and consequences for early pregnancy.	2009	19848282
Studies on fixed-time ovulation induction in the pig.	2009	19848281
Ultrasonographic-guided retrieval and in vitro maturation of eland (Taurotragus oryx) and bongo (Tragelaphus eurycerus isaaci) antelope oocytes.	2009 Apr	18387759
Seasonality, estrous cycle characterization, estrus synchronization, semen cryopreservation, and artificial insemination in the Pacific white-sided dolphin (Lagenorhynchus obliquidens).	2009 Aug	19494046
Measuring fecal progestogens as a tool to monitor reproductive activity in captive female bottlenose dolphins (Tursiops truncatus).	2009 Dec	19783290
Infectivity of porcine circovirus type 2 DNA in semen from experimentally-infected boars.	2009 Jan-Feb	18973743
Effect of altrenogest-treatment of mares in late gestation on adrenocortical function, blood count and plasma electrolytes in their foals.	2009 Jul	19803053
Doping control analysis of trenbolone and related compounds using liquid chromatography-tandem mass spectrometry.	2009 Mar	19007801
The secretions of oviduct epithelial cells increase the equine in vitro fertilization rate: are osteopontin, atrial natriuretic peptide A and oviductin involved?	2009 Nov 19	19925651
Post natal oestrogen administration stimulates precocious endometrial gland development in the horse.	2009 Sep	19927587
Effect of day of transfer and treatment administration on the recipient on pregnancy rates after equine embryo transfer.	2009 Sep	19593666
Oral progestin induces rapid, reversible suppression of ovarian activity in the cat.	2010 Apr 1	20051246
Treatment efficacy of trimethoprim sulfamethoxazole, pentoxifylline and altrenogest in experimentally induced equine placentitis.	2010 Aug	20416936
Induction and synchronization of ovulations of nulliparous and multiparous sows with an injection of gonadotropin-releasing hormone agonist (Receptal).	2010 Feb	19962182
Concentrations of altrenogest in plasma of mares and foals and in allantoic and amniotic fluid at parturition.	2010 Jul 15	20452000
Post-weaning Altrenogest treatment in primiparous sows; the effect of duration and dosage on follicular development and consequences for early pregnancy.	2010 Jun	20223607
Altrenogest treatment during late pregnancy did not reduce colostrum yield in primiparous sows.	2010 May	20118420

Patents

Sample Use Guides

In Vivo Use Guide

for animals only: Administer 6.8 mL (15 mg altrenogest) per gilt once daily for 14 consecutive days.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

ALTRENOGEST

Official Name

English

17.ALPHA.-ALLYL-ESTRA-4,9,11-TRIENE-17.BETA.-OL-3-ONE

Systematic Name

English

RU-2267

Code

English

A-35957

Code

English

altrenogest [INN]

Common Name

English

ESTRA-4,9,11-TRIEN-3-ONE, 17-HYDROXY-17-(2-PROPEN-1-YL)-, (17.BETA.)-

Systematic Name

English

ESTRA-4,9,11-TRIEN-3-ONE, 17.BETA.-HYDROXY-17-(2-PROPENYL)-

Systematic Name

English

ALLYLTRENBOLONE

Common Name

English

ALTRENOGEST [MI]

Common Name

English

NSC-759180

Code

English

17α-Allyl-17-hydroxyestra-4,9,11-trien-3-one

Systematic Name

English

ALTRENOGEST [GREEN BOOK]

Common Name

English

ALTRENOGEST [USAN]

Common Name

English

ALTRENOGEST [MART.]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 556.36