Betamethasone Valerate

HCID 16533
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
2152-44-5
Standard SMILES
CCCCC(=O)O[C@]1(C(=O)CO)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
InChIKey
SNHRLVCMMWUAJD-SUYDQAKGSA-N
Molecular formula
C27H37FO6
Average molar mass
476.6 g/mol
Monoisotopic mass
476.25741712

Overview

Betamethasone valerate is a steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester. It has a role as an anti-inflammatory drug. It is a primary alpha-hydroxy ketone, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a steroid ester, a fluorinated steroid and a 3-oxo-Delta(1),Delta(4)-steroid. It is functionally related to a betamethasone.

Names & identifiers

Preferred name
Betamethasone Valerate
IUPAC
[(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] pentanoate
English name
Betamethasone 17-valerate
Molecular formula
C27H37FO6
Molecular weight
476.58

Names & synonyms

BETAMETHASONE VALERATEBetamethasone 17-valerate2152-44-5Valisonebeta-ValBetadermTokudermLuxiqBetatrexDermabetValnacRinderon V
Show more names
BETNOVATEBETHAMETASONE VALERATEBetoidValison9α-FluoDeviphos
BextasolStanovalDTXSID7022673BettamousseBetamethasone (as valerate)9IFA5XM7R2Betamethasoni valerasNSC-755912

Database identifiers

CAS
2152-44-5
PubChem CID
16533
DTXSID
DTXSID7022673
ChEMBL
CHEMBL1497
ChEBI
CHEBI:31277
UNII
9IFA5XM7R2
EC Number
218-439-3
Nikkaji
J7.337G

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
101 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
7
Rotatable bonds
7
Heavy atoms
34

Experimental & physicochemical properties

DrugsPharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsActive Ingredients (Betamethasone Valerate) -> FDA Greenbook
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section · 2 items

215.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID7022673]

214 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
183 · 183-184°
alpha
77 ° · D +77° (dioxane)
Boiling point
598.9 · 598.9±50.0 °C(Predicted)
Density
1.1174 · 1.1174 (estimate)
storage temp.
2 · 2-8°C
solubility
Practically insoluble in water, freely soluble in acetone and in methylene chloride, soluble in ethanol (96 per cent).

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H330 (35.6%): Fatal if inhaled [Danger Acute toxicity, inhalation]

P203, P260, P264, P270, P271, P273, P280, P284, P304+P340, P316, P318, P319, P320, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 146 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationBetamethasone valerate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16-methyl-17-[(1-oxopentyl)oxy]-, (11.beta.,16.beta.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 2 (35.6%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
WGK 2
rtecs
TU3835000
hs_code
2937229000
Toxicity
mouse,LD50,intraperitoneal,632mg/kg (632mg/kg),Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
risk_code
48

Chemistry & industry

Pharmacology

FDA Pharmacological Classification · 4 items

BETAMETHASONE VALERATE

Corticosteroid Hormone Receptor Agonists [MoA]; Corticosteroid [EPC]

BETAMETHASONE VALERATE FOAM

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

MeSH Pharmacological Classification · 2 items

Substances that reduce or suppress INFLAMMATION.

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.

Uses & manufacturing

Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Applications · 2 items

DescriptionBetamethasone 17-valerate is a synthetic glucocorticoid ester. It is the 17-valerate ester of betamethasone. Betamethasone 17-valerate is often used to treat mild eczema with good efficacy and lower incidence of steroid induced adverse effects due to its lower potency compared to other glucocorticoids. It is available in cream, ointment, lotion, and foam preparations for topical use.

UsesBetamethasone 17-Valerate is a glucocorticoid with anti-inflammatory properties and immunosuppressive activity. It is an antiepileptic non-selective phosphodiesterase inhibitor. Topical application of Betamethasone 17-Valerate has been shown to inhibit heat-induced vasodilatation in man. As a medium-strength corticosteroid, this medication is used to treat a variety of skin conditions (such as eczema, dermatitis, allergies, rash). Betamethasone reduces the swelling, itching, and redness that can occur in these types of conditions.

Upstream & downstream products

Upstream raw materials

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Betamethasone valerate is a steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester. It has a role as an anti-inflammatory drug. It is a steroid ester, a 20-oxo steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid and a primary alpha-hydroxy ketone. It is functionally related to a betamethasone.

Related reactions

1 records
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Compound notes

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