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C6116

Sigma-Aldrich

(+/-)-Cloprostenol sodium salt hydrate

≥98% (HPLC), powder

Synonym(s):

(+/-)-16-(3-Chlorophenoxy)-9,11,15R-trihydroxy-17,18,19,20-tetranorprosta-5Z,13E-dien-1-oic acid sodium salt hydrate

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About This Item

Empirical Formula (Hill Notation):
C22H28ClNaO6 · xH2O
CAS Number:
Molecular Weight:
446.90 (anhydrous basis)
EC Number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

light brown

mp

68-70 °C

solubility

H2O: >10 mg/mL

storage temp.

−20°C

SMILES string

[Na+].[H]O[H].O[C@@H](COc1cccc(Cl)c1)\C=C\[C@H]2[C@H](O)C[C@H](O)[C@@H]2C\C=C/CCCC([O-])=O

InChI

1S/C22H29ClO6.Na.H2O/c23-15-6-5-7-17(12-15)29-14-16(24)10-11-19-18(20(25)13-21(19)26)8-3-1-2-4-9-22(27)28;;/h1,3,5-7,10-12,16,18-21,24-26H,2,4,8-9,13-14H2,(H,27,28);;1H2/q;+1;/p-1/b3-1-,11-10+;;/t16-,18-,19-,20+,21-;;/m1../s1

InChI key

ZEQHRVULQBYULU-LPFHDDPUSA-M

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General description

Cloprostenol is a synthetic analogue of prostaglandin F2α (PGF). Cloprostenol contributes to the induction of estrus in animals and has uterotonic activity. Cloprostenol induces abortion in animals.

Application

(+/-)-Cloprostenol sodium salt hydrate has been used in studying its influence in oestrus synchronisation and uterine development in mice.

Biochem/physiol Actions

Cloprostenol is a potent FP prostanoid receptor agonist. It is 2- to 3-fold more potent than fluprostenol but less selective. Cloprostenol is similar in potency to PGF at EP and TP prostanoid receptors. It is used for the treatment of infertility in sows and gilts.

Features and Benefits

This compound is featured on the Prostanoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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X Valldecabres-Torres et al.
Journal of dairy science, 96(3), 1647-1652 (2013-01-15)
The 6-d timed artificial insemination protocol has been designed to advance luteolysis after the first administration of GnRH so that the preovulatory follicular diameter at second GnRH is reduced and thereby pregnancy outcome may be improved. To achieve an earlier
Mano Sira et al.
Aesthetic surgery journal, 32(7), 822-824 (2012-09-04)
The prostaglandin F2a (PGF2a) analogue bimatoprost 0.03% (Allergan, Inc, Irvine, California) has been employed for the treatment of hypotrichosis since it gained Food and Drug Administration approval as Latisse in 2008. In this report, the authors retrospectively review the cases
New estrus synchronization and artificial insemination protocol for goats based on male exposure, progesterone and cloprostenol during the non-breeding season
Lopez-Sebastian A, et al.
Theriogenology, 68(8), 1081-1087 (2007)
Cloprostenol and eCG influence oestrus synchronisation and uterine development in mice
Wei S, et al.
Veterinarni medicina, 60(1), 31-38 (2015)
Prostaglandin F2α and progesterone release in vitro by ovine luteal tissue during induced luteolysis
Rexroad CE and Guthrie HD
Ovarian follicular and corpus luteum function, 639-644 (1979)

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