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Mupirocin

HCID 446596
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
12650-69-0
표준 SMILES
C/C(=C\C(=O)OCCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O
InChIKey
MINDHVHHQZYEEK-HBBNESRFSA-N
분자식
C26H44O9
평균 분자량
500.6 g/mol
단동위원소 질량
500.29853299

개요

Mupirocin is an alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections. It has a role as an antibacterial drug, a protein synthesis inhibitor and a bacterial metabolite. It is a monocarboxylic acid, a triol, an epoxide, a secondary alcohol, a member of oxanes and an alpha,beta-unsaturated carboxylic ester. It is a conjugate acid of a mupirocin(1-).

이름 및 식별자

우선 이름
Mupirocin
IUPAC
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]oxynonanoic acid
영어명
Mupirocin
분자식
C26H44O9
분자량
500.62

이름 및 동의어

Mupirocin12650-69-0Pseudomonic acidMupirocinePseudomonic acid ACentanyBactodermMupirocinaMupirocinumTurixintrans-Pseudomonic acidBRL 4910A
이름 더 보기
MUPIROCIN CALCIUM231-791-2bactrobanL-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-(2S,3S)-3-(1S,2S)-2-hydroxy-1-methylpropyloxiranylmethyl-3-methyl-, 8-carboxyoctyl ester, (2E)-TurixiMupricin
BRL-4910A9-[(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]oxynonanoic acidDTXSID0046438NSC-759182D0GX863OA5L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, (2E)-CHEBI:7025DTXCID8026438

데이터베이스 식별자

CAS
12650-69-0
PubChem CID
446596

물성

구조 계산 물성보충 중

XLogP
3
극성 표면적
146 Ų
수소 결합 공여자 수
4
수소 결합 수용자 수
9
회전 가능 결합 수
17
무거운 원자 수
35
형식 전하
0
복잡도
694

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

Solubility2.65e-02 g/L
Human Drugs · 4건

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents, Local; Antibacterial Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Dermatological medicines > Anti-infective medicines

Animal DrugsActive Ingredients (Mupirocin) -> FDA Greenbook
Melting Point · 2건

77-78

77 - 78 °C

Physical DescriptionSolid
Collision Cross Section · 2건

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

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

물리화학적 성질

녹는점
77 · 77-780C

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 25% (1 of 4) of reports.

Warning

H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory InformationMupirocin: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (25%)

독성 정보

Adverse EffectsAdverse Drug Reactions
Toxicity Summary · 1건

Currently, no available study or report suggests that using topical mupirocin consistently causes systemic toxicity. As previously stated, caution is advised in individuals with severe renal impairment and those with large open wounds due to the potential for increased absorption and nephrotoxicity. In such cases, renal function should be closely monitored with scheduled renal function panels, as stated in the FDA guidelines for Bactroban.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
2

화학 및 산업

약리 정보

ATC Code · 6건

D06AX09

R - Respiratory system

D - Dermatologicals

QD - Dermatologicals

QR - Respiratory system

D06AX09

Protein BindingThe protein binding of mupirocin is reported to be over 95%.
Pharmacodynamics · 1건

Mupirocin is reported to be active against susceptible aerobic gram-positive cocci, such as _Staphylococcus aureus_, _Staphylococcus epidermidis_, and other beta-hemolytic streptococci_Streptococcus pyogenes_. It mediates its antibacterial activity by inhibiting the bacterial protein synthesis and formation of bacterial proteins essential for survival. The minimum bactericidal concentration (MBC) against relevant pathogens is generally eight-fold to thirty-fold higher than the minimum inhibitory concentration (MIC). In one clinical study investigating the therapeutic effectiveness of topical mupirocin in impetigo, the therapeutic response rate was about 94 to 98% after one week following the end of therapy. In clinical studies of patients with primary and secondary skin infections, both elimination of the bacterial pathogen and clinical cure or improvement hav been demonstrated in over 90% of patients receiving topical mupirocin. Mupirocin resistance as high as 81% has been reported previously. Resistance to mupirocin, which occurs more frequently in methicillin-resistant than methicillin-susceptible staphylococci, may occur with the production of a modified isoleucyl-tRNA synthetase, or the acquisition of, by genetic transfer, a plasmid mediating a new isoleucyl-tRNA synthetase.

Mechanism of Action · 1건

Mupirocin specifically and reversibly binds to bacterial isoleucyl transfer-RNA (tRNA) synthetase, which is an enzyme that promotes the conversion of isoleucine and tRNA to isoleucyl-tRNA. Inhibition of this enzyme subsequently leads to the inhibition of the bacterial protein and RNA synthesis. Mupirocin is bacteriostatic at lower concentrations but it exerts bactericidal effects with prolonged exposure, killing 90-99% of susceptible bacteria over a 24 hour period.

Biological Half-LifeIn healthy male volunteers, the elimination half-life of mupirocin was about 20 to 40 minutes following intravenous administration. The elimination half-life of monic acid was about 30 to 80 minutes.

관련 반응

16건
반응 기록 만들기
HRID 16666 반응식
HRID 16666반응물로uspto-grants-2010_06
HRID 16669 반응식
HRID 16669반응물로uspto-grants-2010_06
HRID 16670 반응식
HRID 16670반응물로uspto-grants-2010_06
HRID 16671 반응식
HRID 16671반응물로uspto-grants-2010_06
HRID 16672 반응식
HRID 16672반응물로uspto-grants-2010_06
HRID 16673 반응식
HRID 16673반응물로uspto-grants-2010_06
HRID 16674 반응식
HRID 16674반응물로uspto-grants-2010_06
HRID 16675 반응식
HRID 16675반응물로uspto-grants-2010_06
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새 노트새 반응견적 요청하기
DTXSID
DTXSID0046438
ChEMBL
CHEMBL719
ChEBI
CHEBI:7025
UNII
D0GX863OA5
EC Number
603-145-3
Nikkaji
J15.623J
끓는 점
672 ℃ · 672℃
밀도
1.183 · 1.183±0.06 g/cm3(Predicted)
인화점
110 ° · >110°(230°F)
저장 조건
-20 °C · Inert atmosphere,Store in freezer, under -20°C
용해도
2 O: · H2O: 12 mg/mL, 가용성
물리적 상태
고체
산도 계수 (pKa)
4.78 · 4.78±0.10(Predicted)
색상
흰색에서 황갈색까지
수용성
DMSO 또는 메탄올에 용해됩니다. 물에 거의 녹지 않음
Merck
14 · 14,6302
안정성
1 · 제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO의 솔루션은 -20°C에서 최대 1개월 동안 보관할 수 있습니다.
주요 응용
제약
InChIKey
MINDHVHHQZYEEK-HBBNESRFSA-N
SMILES
[H][C@@]1(CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O)C[C@@H]2O[C@@]2([H])[C@@H](C)[C@H](C)O

화학적 성질

White Crystalline Solid

rtecs
RA6907000
HS 번호
2941906000
스토리지 클래스
11 - Combustible Solids
Metabolism/MetabolitesFollowing intravenous or oral administration, mupirocin undergoes rapid hepatic metabolism to form the principal metabolite monic acid, which has no antibacterial activity.
FDA Pharmacological Classification · 6건

D0GX863OA5

MUPIROCIN

Established Pharmacologic Class [EPC] - RNA Synthetase Inhibitor Antibacterial

Mechanisms of Action [MoA] - RNA Synthetase Inhibitors

Mupirocin is a RNA Synthetase Inhibitor Antibacterial. The mechanism of action of mupirocin is as a RNA Synthetase Inhibitor.

MUPIROCIN

MeSH Pharmacological Classification · 2건

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.

Substances that inhibit the growth or reproduction of BACTERIA.

Absorption, Distribution and Excretion · 4건

Systemic or percutaneous absorption of mupirocin following dermal application is expected to be minimal in adults and children. Occlusive dressings do not significantly enhance drug absorption, but damaged skin may allow enhanced penetration of the drug across the skin barrier.

Any mupirocin reaching the systemic circulation is rapidly metabolized to form the inactive monic acid, which is eliminated by renal excretion. Following the application of Centany (mupirocin ointment),2% to a 400 cm2 area on the back of 23 healthy volunteers once daily for 7 days, the mean (range) cumulative urinary excretion of monic acid over 24 hrs following the last administration was 1.25% (0.2% to 3.0%) of the administered dose of mupirocin.

No information available.

No information available.

Cellular LocationsCytoplasm

용도 및 제조

UsesUse (kg; approx.) in Germany (2009): >50
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

응용 분야

개요Mupirocin (pseudomonic acid A) is an antibiotic produced by Pseudomonas fluorescens. It is useful in the treatment of dermal infections, especially those involving S. aureus and S. epidermidis.

용도Mupirocin, is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial.

상·하류 제품 정보

상류 원료

망간 돕 실리실릭산(H4SiO4) 아연염(1:2)
추가 설명 · 1건

정의ChEBI: An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2 -pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydro ybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.