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Merck

C6116

Sigma-Aldrich

(+/-)-Cloprostenol sodium salt hydrate

≥98% (HPLC), powder

Sinónimos:

(+/-)-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

Fórmula empírica (notación de Hill):
C22H28ClNaO6 · xH2O
Número de CAS:
Peso molecular:
446.90 (anhydrous basis)
EC Number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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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)
M C García Mitacek et al.
Reproduction in domestic animals = Zuchthygiene, 47 Suppl 6, 200-203 (2013-01-04)
The objective of this study was to evaluate the efficacy of cloprostenol (CLO) or aglepristone (ALI) for pregnancy termination in queens at 21-22 and 35-38 days of gestation. Two experiments (EXP) were carried out to accomplish this aim. Thirty-seven 12-
Iwona Dams et al.
Chirality, 25(3), 170-179 (2013-02-06)
The 17-phenyl PGF(2α) analogue bimatoprost (10a) is the most efficacious ocular hypotensive agent currently available for the treatment of glaucoma or ocular hypertension. A novel convergent synthesis of 13,14-en-15-ol prostamideF(2α) analogues was developed employing Julia-Lythgoe olefination of the structurally advanced
Muhammad Modu Bukar et al.
Reproductive biology, 12(3), 325-328 (2012-11-17)
The effects of estrus synchronization with prostaglandin F(2α) (PGF(2α)) and Controlled Internal Drug Release Device (CIDR) on ensuing antral follicular development were documented and compared to natural estrous cycles of non-seasonal tropical goats. Two to six follicular waves were observed
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

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