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HCID 8982Erstellt: 27. Oktober 2026

Nafcillin

C07250 · Nafcilin 1 · Nafcillin acid · Westwood acid, naphthalene · Nafcillin Powder USP Standard · 6α-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]penicillanic acid · 6-(2-Ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid · (2S,5R,6R)-6-(2-Ethoxy-1-naphthoylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

https://huagongshe.com/de/chemical/8982

Identifikatoren & physikalische Daten

CAS No.	147-52-4
Summenformel	C21H22N2O5S
Durchschnittliche Molmasse	414,5 g/mol
Monoisotopische Masse	414,12494298 g/mol
SMILES	CCOc1ccc2ccccc2c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O
InChIKey	GPXLMGHLHQJAGZ-JTDSTZFVSA-N
PubChem CID	8982
ChEMBL	CHEMBL1443
ChEBI	CHEBI:7447
EC No.	205-690-9
DTXSID	DTXSID8023343
Lokaler Name	Nafcillin

Chemische & physikalische Eigenschaften

XLogP	2,9
Polarare Oberfläche (TPSA)	121
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	6
Frei drehbare Bindungen	5
Schwere Atome	29
Formalladung	0
Komplexität	699
Arzneimittel	Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics
LogP (Verteilungskoeffizient)	3.3
Löslichkeit	SolubleNOT MORE THAN SLIGHT CHARACTERISTIC ODORWHITE TO YELLOWISH WHITE POWDERFREELY SOL IN WATER & CHLOROFORM, SOL IN ALCOHOL /NAFCILLIN SODIUM/1.72e-02 g/L
Human Drugs	Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsPenicillinsPharmaceuticalsAccess group antibiotics
Physical Description	Solid
Stability/Shelf Life	STABLE @ ROOM TEMP FOR 2-4 YR /DRY STATE/ DEPENDING ON DOSAGE FORMORAL SOLN AFTER RECONSTITUTION WITH DILUENT SHOULD BE STORED @ 2-8 °C /DISCARD UNUSED SOLN AFTER 1 WK/STABLE FOR 24 HR IN 1/6 MOLAR SODIUM LACTATE INJECTION WHEN STORED @ ROOM TEMP IN CONCN OF 30 MG/MLLESS THAN 10% ACTIVITY LOST @ ROOM TEMP IN 24 HR (0.905% SODIUM CHLORIDE, 5% DEXTROSE IN 0.45% SODIUM CHLORIDE OR RINGER SOLN)For more Stability/Shelf Life (Complete) data for NAFCILLIN (10 total), please visit the HSDB record page.
Collision Cross Section	202 Å² [M+Na]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]197.59 Å² [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Siedepunkt	714.1±60.0 °C(Predicted)
Dichte	1.42±0.1 g/cm3(Predicted)
pKa (Säurekonstante)	2.44±0.50(Predicted)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen	REACH registered substance: Nafcillin (EC: 205-690-9)
FDA-Anforderungen	Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).
Hazard Classes and Categories	Skin Sens. 1 (100%)
Lagerbedingungen	Commercially available nafcillin sodium capsules and tablets should be stored in tight containers at a temperature less than 40 °C, preferably between 15-30 °Cthe tablets should also be protected from light. /Nafcillin sodium/Nafcillin sodium powder for injection should be stored @ room temperature or colder. /Nafcillin sodium/
Entsorgungsverfahren	SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Wechselwirkungen	SERUM BINDING OF...NAFCILLIN...IS REDUCED WHEN ADMIN CONCURRENTLY WITH ASPIRIN.CHLORAMPHENICOL MAY ANTAGONIZE ACTION OF PENICILLINS. /PENICILLINS/...ALL...PENICILLINS & ERYTHROMYCINS MAY THEORETICALLY BE EXPECTED TO.../EXHIBIT SYNERGISTIC ANTIBACTERIAL ACTIVITY/. /PENICILLINS/TETRACYCLINE MAY ANTAGONIZE BACTERICIDAL EFFECT OF PENICILLIN /G/...ANTAGONISM OF ACTION OF ALL...PENICILLINS MIGHT BE EXPECTED. /PENICILLINS/For more Interactions (Complete) data for NAFCILLIN (14 total), please visit the HSDB record page.
Hepatotoxicity	Only rare instances of clinically apparent hepatotoxicity have been linked touse of nafcillin. Typically, the injury is a cholestatic hepatitis thatarises 1 to 6 weeks after starting nafcillin and can be prolonged butultimately resolves. Rash, fever, and eosinophilia are uncommon but canoccur (Case 1). The injury is much like that described with flucloxacillinand cloxacillin but is less frequent with nafcillin. Autoantibodies areuncommon. These favorable outcomes are typical but not invariable. At leastone instance of acute liver failure and one with persistent cholestasis andvanishing bile duct syndrome have been reported. Interestingly, thepersistent serum aminotransferase elevations that are common during highdose intravenous therapy with oxacillin appear to be rare with high doses ofintravenous nafcillin. In several reports of patients who developed elevatedserum aminotransferase levels while on high dose oxacillin, switching tointravenous nafcillin or other penicillin antibiotics was done withoutrecurrence of the liver injury. This may relate to the peak doses chosen forintravenous oxacillin versus nafcillin.
Medical Surveillance	Renal, hepatic, and hematologic systems should be evaluated periodically during prolonged therapy with nafcillin. Because adverse hematologic effects have occurred during therapy with penicillinase-resistant penicillins, total and differential leukocyte counts should be performed prior to initiation of therapy and 1-3 times weekly during therapy. In addition, urinalysis should be performed and BUN and serum creatinine, AST (SCOT), and ALT (SGPT) concn should be determined prior to and periodically during therapy.
Human Toxicity Excerpts	SEE PENICILLINS. MASSIVE IV DOSES...(20-60 MILLION UNITS/DAY...) MAY RESULT IN ENCEPHALOPATHY WITH MUSCULAR HYPERIRRITABILITY, MYOCLONUS, VISUAL & AUDITORY HALLUCINATIONS & GENERALIZED CONVULSIONS. /PENICILLINS/OF 29 STAPH AUREUS PATIENTS TREATED WITH 12 G/DAY IV NAFCILLIN, 4 HAD FEVER, RASH, & LEUKOPENIA1 HAD ABSOLUTE NEUTROPENIA.EFFECT IS MOST LIKELY DUE TO DIRECT TOXIC EFFECT ON BONE MARROW. USUALLY OCCURS DURING 3RD WK THERAPY & REMITS WITH DRUG CESSATION.HYPOKALEMIA WAS ASSOCIATED WITH NAFCILLIN ADMINISTRATION.For more Human Toxicity Excerpts (Complete) data for NAFCILLIN (46 total), please visit the HSDB record page.
Drug Induced Liver Injury	Drug-Induced Liver Injury Severity and Toxicity (DILIst)nafcillinDILI PositiveIntravenousDOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts	IN MICE, RATS, RABBITS...DEATH FROM RESP FAILURE WITH OR WITHOUT CONVULSIONS OCCURRED 6-18 HR AFTER SINGLE ORAL DOSES. ACUTE GASTROENTERITIS & CARDIOVASCULAR SHOCK WERE ASSOC PHENOMENA. /PENICILLINS//IN GUINEA PIGS,/ DEATH FROM RESP FAILURE WITH OR WITHOUT CONVULSIONS OCCURRED 6-18 HR AFTER SINGLE ORAL DOSES. ACUTE GASTROENTERITIS & CARDIOVASCULAR SHOCK... ALSO...A LATE (1-2 WK) & GRADUALLY DEVELOPING TOXEMIA KILLED ALL SURVIVORS OF ACUTE RESPONSE. /PENICILLINS/IN HAMSTERS THE DRUG IS SOMEWHAT MORE TOXIC BY THE ORAL THAN BY THE SC ROUTE WHEN OBSERVED FOR 14 DAYS AFTER SINGLE DOSES. TOLERANCE DEVELOPED TO MULTIPLE DOSING. PERHAPS THE SENSITIVITY OF GUINEA PIGS IS RELATED TO EFFECTS ON INTESTINAL MICROFLORA. /PENICILLINS/...CATS & DOGS...DEATH FROM RESP FAILURE WITH OR WITHOUT CONVULSIONS OCCURRED 6-18 HR AFTER SINGLE ORAL DOSES. ACUTE GASTROENTERITIS & CARDIOVASCULAR SHOCK WERE ASSOC PHENOMENA. /PENICILLINS/For more Non-Human Toxicity Excerpts (Complete) data for NAFCILLIN (6 total), please visit the HSDB record page.
Effects During Pregnancy and Lactation	◉ Summary of Use during Lactation
Gefahrstoffdaten	147-52-4(Hazardous Substances Data)

Anwendungen & Verwendung

Verwenden

Antibacterial.

Nafcillin

Identifikatoren & physikalische Daten

CAS No.

147-52-4

Summenformel

C21H22N2O5S

Durchschnittliche Molmasse

414,5 g/mol

Monoisotopische Masse

414,12494298 g/mol

SMILES

CCOc1ccc2ccccc2c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O

InChIKey

GPXLMGHLHQJAGZ-JTDSTZFVSA-N

PubChem CID

8982

ChEMBL

CHEMBL1443

ChEBI

CHEBI:7447

EC No.

205-690-9

DTXSID

DTXSID8023343

Lokaler Name

Nafcillin

Chemische & physikalische Eigenschaften

XLogP

2,9

Polarare Oberfläche (TPSA)

121

H-Brücken-Donoren

H-Brücken-Akzeptoren

Frei drehbare Bindungen

Schwere Atome

Formalladung

Komplexität

699

Arzneimittel

Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics

LogP (Verteilungskoeffizient)

3.3

Löslichkeit

SolubleNOT MORE THAN SLIGHT CHARACTERISTIC ODORWHITE TO YELLOWISH WHITE POWDERFREELY SOL IN WATER & CHLOROFORM, SOL IN ALCOHOL /NAFCILLIN SODIUM/1.72e-02 g/L

Human Drugs

Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsPenicillinsPharmaceuticalsAccess group antibiotics

Physical Description

Solid

Stability/Shelf Life

STABLE @ ROOM TEMP FOR 2-4 YR /DRY STATE/ DEPENDING ON DOSAGE FORMORAL SOLN AFTER RECONSTITUTION WITH DILUENT SHOULD BE STORED @ 2-8 °C /DISCARD UNUSED SOLN AFTER 1 WK/STABLE FOR 24 HR IN 1/6 MOLAR SODIUM LACTATE INJECTION WHEN STORED @ ROOM TEMP IN CONCN OF 30 MG/MLLESS THAN 10% ACTIVITY LOST @ ROOM TEMP IN 24 HR (0.905% SODIUM CHLORIDE, 5% DEXTROSE IN 0.45% SODIUM CHLORIDE OR RINGER SOLN)For more Stability/Shelf Life (Complete) data for NAFCILLIN (10 total), please visit the HSDB record page.

Collision Cross Section

202 Å² [M+Na]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]197.59 Å² [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]

Siedepunkt

714.1±60.0 °C(Predicted)

Dichte

1.42±0.1 g/cm3(Predicted)

pKa (Säurekonstante)

2.44±0.50(Predicted)

Sicherheit & Vorschriften

GHS-Einstufung

DangerH317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Regulatorische Informationen

REACH registered substance: Nafcillin (EC: 205-690-9)

FDA-Anforderungen

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).

Hazard Classes and Categories

Skin Sens. 1 (100%)

Lagerbedingungen

Commercially available nafcillin sodium capsules and tablets should be stored in tight containers at a temperature less than 40 °C, preferably between 15-30 °Cthe tablets should also be protected from light. /Nafcillin sodium/Nafcillin sodium powder for injection should be stored @ room temperature or colder. /Nafcillin sodium/

Entsorgungsverfahren

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Wechselwirkungen

SERUM BINDING OF...NAFCILLIN...IS REDUCED WHEN ADMIN CONCURRENTLY WITH ASPIRIN.CHLORAMPHENICOL MAY ANTAGONIZE ACTION OF PENICILLINS. /PENICILLINS/...ALL...PENICILLINS & ERYTHROMYCINS MAY THEORETICALLY BE EXPECTED TO.../EXHIBIT SYNERGISTIC ANTIBACTERIAL ACTIVITY/. /PENICILLINS/TETRACYCLINE MAY ANTAGONIZE BACTERICIDAL EFFECT OF PENICILLIN /G/...ANTAGONISM OF ACTION OF ALL...PENICILLINS MIGHT BE EXPECTED. /PENICILLINS/For more Interactions (Complete) data for NAFCILLIN (14 total), please visit the HSDB record page.

Hepatotoxicity

Only rare instances of clinically apparent hepatotoxicity have been linked touse of nafcillin. Typically, the injury is a cholestatic hepatitis thatarises 1 to 6 weeks after starting nafcillin and can be prolonged butultimately resolves. Rash, fever, and eosinophilia are uncommon but canoccur (Case 1). The injury is much like that described with flucloxacillinand cloxacillin but is less frequent with nafcillin. Autoantibodies areuncommon. These favorable outcomes are typical but not invariable. At leastone instance of acute liver failure and one with persistent cholestasis andvanishing bile duct syndrome have been reported. Interestingly, thepersistent serum aminotransferase elevations that are common during highdose intravenous therapy with oxacillin appear to be rare with high doses ofintravenous nafcillin. In several reports of patients who developed elevatedserum aminotransferase levels while on high dose oxacillin, switching tointravenous nafcillin or other penicillin antibiotics was done withoutrecurrence of the liver injury. This may relate to the peak doses chosen forintravenous oxacillin versus nafcillin.

Medical Surveillance

Renal, hepatic, and hematologic systems should be evaluated periodically during prolonged therapy with nafcillin. Because adverse hematologic effects have occurred during therapy with penicillinase-resistant penicillins, total and differential leukocyte counts should be performed prior to initiation of therapy and 1-3 times weekly during therapy. In addition, urinalysis should be performed and BUN and serum creatinine, AST (SCOT), and ALT (SGPT) concn should be determined prior to and periodically during therapy.

Human Toxicity Excerpts

SEE PENICILLINS. MASSIVE IV DOSES...(20-60 MILLION UNITS/DAY...) MAY RESULT IN ENCEPHALOPATHY WITH MUSCULAR HYPERIRRITABILITY, MYOCLONUS, VISUAL & AUDITORY HALLUCINATIONS & GENERALIZED CONVULSIONS. /PENICILLINS/OF 29 STAPH AUREUS PATIENTS TREATED WITH 12 G/DAY IV NAFCILLIN, 4 HAD FEVER, RASH, & LEUKOPENIA1 HAD ABSOLUTE NEUTROPENIA.EFFECT IS MOST LIKELY DUE TO DIRECT TOXIC EFFECT ON BONE MARROW. USUALLY OCCURS DURING 3RD WK THERAPY & REMITS WITH DRUG CESSATION.HYPOKALEMIA WAS ASSOCIATED WITH NAFCILLIN ADMINISTRATION.For more Human Toxicity Excerpts (Complete) data for NAFCILLIN (46 total), please visit the HSDB record page.

Drug Induced Liver Injury

Drug-Induced Liver Injury Severity and Toxicity (DILIst)nafcillinDILI PositiveIntravenousDOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity Excerpts

IN MICE, RATS, RABBITS...DEATH FROM RESP FAILURE WITH OR WITHOUT CONVULSIONS OCCURRED 6-18 HR AFTER SINGLE ORAL DOSES. ACUTE GASTROENTERITIS & CARDIOVASCULAR SHOCK WERE ASSOC PHENOMENA. /PENICILLINS//IN GUINEA PIGS,/ DEATH FROM RESP FAILURE WITH OR WITHOUT CONVULSIONS OCCURRED 6-18 HR AFTER SINGLE ORAL DOSES. ACUTE GASTROENTERITIS & CARDIOVASCULAR SHOCK... ALSO...A LATE (1-2 WK) & GRADUALLY DEVELOPING TOXEMIA KILLED ALL SURVIVORS OF ACUTE RESPONSE. /PENICILLINS/IN HAMSTERS THE DRUG IS SOMEWHAT MORE TOXIC BY THE ORAL THAN BY THE SC ROUTE WHEN OBSERVED FOR 14 DAYS AFTER SINGLE DOSES. TOLERANCE DEVELOPED TO MULTIPLE DOSING. PERHAPS THE SENSITIVITY OF GUINEA PIGS IS RELATED TO EFFECTS ON INTESTINAL MICROFLORA. /PENICILLINS/...CATS & DOGS...DEATH FROM RESP FAILURE WITH OR WITHOUT CONVULSIONS OCCURRED 6-18 HR AFTER SINGLE ORAL DOSES. ACUTE GASTROENTERITIS & CARDIOVASCULAR SHOCK WERE ASSOC PHENOMENA. /PENICILLINS/For more Non-Human Toxicity Excerpts (Complete) data for NAFCILLIN (6 total), please visit the HSDB record page.

Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Gefahrstoffdaten

147-52-4(Hazardous Substances Data)