Mupirocin (calcium hydrate)

CAT: 0804-HY-N7068-01Size: 25 mgDry Ice: NoHazardous: No

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Description

Mupirocin (BRL-4910A, Pseudomonic acid) calcium hydrate is an orally active antibiotic isolated from Pseudomonas fluorescens. Mupirocin calcium hydrate apparently exerts its antimicrobial activity by reversibly inhibiting isoleucyl-transfer RNA, thereby inhibiting bacterial protein and RNA synthesis[1][2].

CAS Number

115074-43-6

Product Name Alternative

BRL-4910A (calcium hydrate) ; Pseudomonic acid (calcium hydrate)

UNSPSC

12352005

Hazard Statement

H302-H312-H332

Target

Antibiotic; Bacterial

Type

Natural Products

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/mupirocin-calcium-hydrate.html

Concentration

10mM

Purity

98.05

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

C[C@H](O)[C@H](C)[C@@]1([H])[C@H](C[C@@]2([H])CO[C@@H](C/C(C)=C/C(OCCCCCCCCC(O)=O)=O)[C@H](O)[C@@H]2O)O1.[H]O[H].[1/2Ca]

Molecular Formula

C26H44O9.1/2Ca.H2O

Molecular Weight

538.68

Precautions

P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

References & Citations

[5]Giacometti A, et al. Mupirocin prophylaxis against methicillin-susceptible, methicillin-resistant, or vancomycin-intermediate Staphylococcus epidermidis vascular-graft infection. Antimicrob Agents Chemother. 2000 Oct. 44 (10) :2842-4.|[1]Sutherland R, et al. Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use. Antimicrob Agents Chemother. 1985 Apr;27 (4) :495-8.|[2]Parenti MA, et al. Mupirocin: a topical antibiotic with a unique structure and mechanism of action. Clin Pharm. 1987 Oct;6 (10) :761-70.|[3]Vingsbo Lundberg C, et al. Efficacy of topical and systemic antibiotic treatment of meticillin-resistant Staphylococcus aureus in a murine superficial skin wound infection model. Int J Antimicrob Agents. 2013 Sep. 42 (3) :272-5.|[4]Mohammad H, Abutaleb NS, Dieterly AM, Lyle LT, Seleem MN. Investigating auranofin for the treatment of infected diabetic pressure ulcers in mice and dermal toxicity in pigs. Sci Rep. 2021 May 25;11 (1) :10935.

Shipping Conditions

Room Temperature

Storage Conditions

4°C (Powder, sealed storage, away from moisture and light)

Scientific Category

Natural Products

Clinical Information

Launched

Chemical Information

Mupirocin Calcium

Mupirocin calcium hydrate is a hydrate that is the dihydrate form of mupirocin calcium. It is an antibacterial drug used for the treatment of skin infections such as impetigo caused by Staphylococcus aureus and meticillin-resistant Staphylococcus aureus (MRSA). It has a role as an antiinfective agent, an antibacterial drug and a protein synthesis inhibitor. It contains a mupirocin calcium (anhydrous).

CAS Number	115074-43-6
PubChem CID	5282317
IUPAC Name	calcium;bis(9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoate);dihydrate
Molecular Formula	C52H90CaO20
Molecular Weight	1075.3
Topological Polar Surface Area	300
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	32
Heavy Atom Count	73
Formal Charge	0
Complexity	689

SMILES

C[C@@H]([C@@H](O)C)[C@@H]1O[C@H]1C[C@@H]2[C@H]([C@H]([C@@H](OC2)C/C(=C/C(=O)OCCCCCCCCC(=O)[O-])/C)O)O.C[C@@H]([C@@H](O)C)[C@@H]1O[C@H]1C[C@@H]2[C@H]([C@H]([C@@H](OC2)C/C(=C/C(=O)OCCCCCCCCC(=O)[O-])/C)O)O.O.O.[Ca+2]

InChI

InChI=1S/2C26H44O9.Ca.2H2O/c2*1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27;;;/h2*13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29);;2*1H2/q;;+2;;/p-2/b2*16-13+;;;/t2*17-,18-,19-,20-,21-,24+,25-,26-;;;/m00.../s1

InChIKey

DDHVILIIHBIMQU-YJGQQKNPSA-L

Chemical Structure

2D Structure

CAS: 115074-43-6

CID: 5282317

Formula: C52H90CaO20

MW: 1075.3

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	1075.3
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	32
Exact Mass	1074.5651361
Monoisotopic Mass	1074.5651361
Topological Polar Surface Area	300 Å²
Heavy Atom Count	73
Formal Charge	0
Complexity	689
Isotope Atom Count	0
Defined Atom Stereocenter Count	16
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	5
Compound Is Canonicalized	Yes

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Catalog	Name
GTR19167266-01	Mupirocin calcium hydrate
C6500-50	Mupirocin calcium
sc-477645A	Mupirocin Calcium Salt
574479	Mupirocin calcium dihydrate

Mupirocin (calcium hydrate)

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