nafcillin

Modify Date: 2026-07-16 19:02:35

nafcillin Structure
nafcillin structure
Common Name nafcillin
CAS Number 147-52-4 Molecular Weight 414.475
Density 1.4±0.1 g/cm3 Boiling Point 714.1±60.0 °C at 760 mmHg
Molecular Formula C21H22N2O5S Melting Point N/A
MSDS N/A Flash Point 385.7±32.9 °C

 Use of nafcillin


Nafcillin, an antibiotic, is a reversible inhibitor of β-lactamase. Nafcillin exhibits bactericidal activity, and can be used for the research of staphylococcal infections[1][2][3][4].

 Names

This table lists Chinese names, IUPAC names and various aliases of this chemical substance.

Name nafcillin
Synonym More Synonyms

 nafcillin Biological Activity

This table contains bioactivity, target information and biological‑assay experimental data of this compound.

Description Nafcillin, an antibiotic, is a reversible inhibitor of β-lactamase. Nafcillin exhibits bactericidal activity, and can be used for the research of staphylococcal infections[1][2][3][4].
Related Catalog
In Vivo Nafcillin (100 mg/kg; s.c.) exhibits bactericidal activity against methicillin-susceptible Staphylococcus aureus (MSSA) and methicillin-resistant S. aureus (MRSA), with MICs of 0.5 μg/mL and 64.0 μg/mL for S. aureus strains Xen-29 and Xen-1, respectively, in mice[3].
References

[1]. Tan, A.K., et al. Identification of the site of covalent attachment of nafcillin, a reversible suicide inhibitor of beta-lactamase. Biochem J, 1992. 281 ( Pt 1): p. 191-6.

[2]. Palmer, D.L., et al. Bacterial wound colonization after broad-spectrum versus narrow-spectrum antibiotics. Ann Thorac Surg, 1995. 59(3): p. 626-31.

[3]. Lawrence I. Mortin, et al. Rapid Bactericidal Activity of Daptomycin against Methicillin-Resistant and Methicillin-Susceptible Staphylococcus aureus Peritonitis in Mice as Measured with Bioluminescent Bacteria. Antimicrob Agents Chemother. 2007 May; 51(5): 1787-1794.

[4]. Sakoulas G, et al. Nafcillin enhances innate immune-mediated killing of methicillin-resistant Staphylococcus aureus. J Mol Med (Berl). 2014 Feb;92(2):139-49.

 Chemical & Physical Properties

This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.

Density 1.4±0.1 g/cm3
Boiling Point 714.1±60.0 °C at 760 mmHg
Molecular Formula C21H22N2O5S
Molecular Weight 414.475
Flash Point 385.7±32.9 °C
Exact Mass 414.124939
PSA 121.24000
LogP 3.52
Vapour Pressure 0.0±2.4 mmHg at 25°C
Index of Refraction 1.686
InChIKey GPXLMGHLHQJAGZ-JTDSTZFVSA-N
SMILES CCOc1ccc2ccccc2c1C(=O)NC1C(=O)N2C1SC(C)(C)C2C(=O)O

 Toxicological Information

This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XI0120000
CHEMICAL NAME :
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-ethoxy-1-naphthamido)-3,3- dimethyl-7-oxo-
CAS REGISTRY NUMBER :
147-52-4
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C21-H22-N2-O5-S
MOLECULAR WEIGHT :
414.51

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
1050 mg/kg/1W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - interstitial nephritis
REFERENCE :
JAMAAP JAMA, Journal of the American Medical Association. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1883- Volume(issue)/page/year: 225,178,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3659 No. of Facilities: 199 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 11979 (estimated) No. of Female Employees: 9552 (estimated)

 Precursor & DownStream

This table lists upstream starting materials and downstream derivative products related to this chemical.

Precursor  3

DownStream  0

 Synonyms

This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.

Propizepina
6-(2-dimethylamino-propyl)-6,11-dihydro-benzo[b]pyrido[2,3-e][1,4]diazepin-5-one
6-(2-Ethoxy-naphth-1-yl-formamino)penicillansaeure
nafcillinum [INN_la]
(2S,5R,6R)-6-({[2-(ethyloxy)naphthalen-1-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Propizepinum
(2-ethoxy-naphthalen-1-yl)-penicillin
[2S-(2a,5a,6b)]-6-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid
Naftopen
Nallpen
Propizepinum [INN-Latin]
6-(2-Ethoxy-1-naphthamido)penicillin
Propizepina [INN-Spanish]
Vagran 50 Kapseln
Propizepine
(2S,5R,6R)-6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

 nafcillin | FAQ

This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.

Q: What is the LogP of nafcillin?
A: LogP of nafcillin is 3.52.
Q: What is the polar surface area (PSA) of nafcillin?
A: Polar surface area (PSA) of nafcillin is 121.24000.
Q: What is the InChIKey of nafcillin?
A: InChIKey of nafcillin is GPXLMGHLHQJAGZ-JTDSTZFVSA-N.
Q: What are the upstream materials of nafcillin?
A: Related upstream materials(CAS) of nafcillin: 27605-28-3;551-16-6;55150-29-3.
Q: What is the English name of nafcillin?
A: The English name of nafcillin is nafcillin.
Q: What is the boiling point of nafcillin?
A: Boiling point of nafcillin is 714.1±60.0 °C at 760 mmHg.
Q: What is the CAS number of nafcillin?
A: CAS number of nafcillin is 147-52-4.
Q: What is the SMILES notation of nafcillin?
A: SMILES notation of nafcillin is CCOc1ccc2ccccc2c1C(=O)NC1C(=O)N2C1SC(C)(C)C2C(=O)O.
Q: What is the molecular weight of nafcillin?
A: Molecular weight of nafcillin is 414.475.
Q: What is the molecular formula of nafcillin?
A: Molecular formula of nafcillin is C21H22N2O5S.
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