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Antibiotics and anti-infectives

Nafcillin

Also known as Naphcillin, Nafcilina, Nafcilline

CAS 147-52-4Formula C21H22N2O5SMolar mass 414.48 g/molEC 205-690-9
GHS signal word: Danger. Pictograms: Harmful or irritant, Serious health hazard 32 suppliers listed Drug substance
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Nafcillin chemical structure, C21H22N2O5S, CAS 147-52-4
2D chemical structure

Key facts

What buyers check first

All properties
CAS number
147-52-4
Formula
C21H22N2O5S
Molar mass
414.48 g/mol
Solubility
NOT MORE THAN SLIGHT CHARACTERISTIC ODOR, WHITE TO YELLOWISH WHITE POWDER, FREELY SOL IN…
HS code
294110
Category
Antibiotics and anti-infectives

What is Nafcillin?

Plain description, key identifiers and synonyms

Nafcillin is a penicillin in which the substituent at position 6 of the penam ring is a (2-ethoxy-1-naphthoyl)amino group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a nafcillin(1-).

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS number
147-52-4 CAS number cross-checkedOther or deprecated CAS: 985-16-0
EC number
205-690-9
Molecular formula
C21H22N2O5S
UNII
4CNZ27M7RV
InChIKey
GPXLMGHLHQJAGZ-JTDSTZFVSA-N
InChI
InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1
Canonical SMILES
CCOc1ccc2ccccc2c1C(=O)NC1C(=O)N2C1SC(C)(C)C2C(=O)O
Isomeric SMILES
CCOC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O

Synonyms

  • Naphcillin
  • Nafcilina
  • Nafcilline
  • Nafcillinum
  • Nafcilin-1
  • (2-Ethoxy-1-naphthyl)penicillin
  • (2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2-ethoxy-1-naphthalenyl)penicillin
  • Penicillin, (2-ethoxy-1-naphthalenyl)-
  • Penicillin, (2-ethoxy-1-naphthyl)-
  • 6-(2-ethoxy-1-naphthamido)penicillanic acid
  • (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-
  • Naphthamidopenicillin
  • (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
  • nafcillina
  • (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
  • (2S,5R,6R)-6-((2-ethoxynaphthalene-1-carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • Nafcillin sodium salt
  • Nafcillin (INN)
  • Nafcillin & VRC3375
  • (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
Show all 26 synonyms
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Solubility
NOT MORE THAN SLIGHT CHARACTERISTIC ODOR, WHITE TO YELLOWISH WHITE POWDER, FREELY SOL IN WATER & CHLOROFORM, SOL IN ALCOHOL /NAFCILLIN SODIUM/exp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
414.48 g/molcalc.
Exact mass
414.1249 Dacalc.
LogP (octanol/water)
2.48calc.
Topological polar surface area
95.94 Ųcalc.
Hydrogen bond donors
2calc.
Hydrogen bond acceptors
5calc.
Rotatable bonds
5calc.
Heavy atoms
29calc.
Rings
4calc.
Aromatic rings
2calc.
Fraction sp3 carbons
0.38calc.
Formal charge
0calc.
Stereocentres
3calc.
Lipinski rule of five
Passes (0 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, O=C(NC1C(=O)N2CCSC12)c1cccc2ccccc12

O=C(NC1C(=O)N2CCSC12)c1cccc2ccccc12

4 rings, 21 atoms.

5 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Danger
GHS07: Harmful or irritant
Harmful or irritant
GHS08: Serious health hazard
Serious health hazard

Hazard statements

  • H317May cause an allergic skin reaction.
  • H334May cause allergy or asthma symptoms or breathing difficulties if inhaled.
Precautionary statements (15)
  • P233Keep container tightly closed.
  • P260Do not breathe dust, fume, gas, mist, vapours or spray.
  • P261Avoid breathing dust, fume, gas, mist, vapours or spray.
  • P271Use only outdoors or in a well-ventilated area.
  • P272Contaminated work clothing should not be allowed out of the workplace.
  • P280Wear protective gloves, protective clothing, eye protection and face protection.
  • P284In case of inadequate ventilation wear respiratory protection.
  • P302 + P352If on skin: Wash with plenty of water.
  • P304 + P340If inhaled: Remove person to fresh air and keep comfortable for breathing.
  • P321Specific treatment (see supplemental first aid instructions on the label).
  • P333 + P317If skin irritation or rash occurs: Get medical help.
  • P342 + P316If experiencing respiratory symptoms: Get emergency medical help immediately.
  • P362 + P364Take off contaminated clothing. And wash it before reuse.
  • P403Store in a well-ventilated place.
  • P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Nafcillin suppliers

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All 32 suppliers
30 of 30 offers
  • Online Pills Store
    United States ManufacturerUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • 001Chemical
    China, HangzhouUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • 3WAY Pharm Inc
    China, ShanghaiUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • Aa Blocks LLC
    United States, San DiegoUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • AbaChemScene, LLC
    United States, Monmouth JunctionUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • AHH Chemical co.,ltd
    China, ChangzhouUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • AKos Consulting & Solutions
    Germany, LorrachUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • Alfa Chemistry
    United States, HolbrookUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • Angene Chemical
    China, NanjingUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
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  • BenchChem
    United States, AustinUnclaimed profile
    NafcillinGrade, purity and minimum order on request
    Price on request
    View

Suppliers marked Unclaimed profile have not claimed their profile yet. They are not verified by CompoundList, their offers are price on request and details may have changed, so please confirm them with the supplier. Company representatives can claim a profile with a business email on the company's own website domain. Our team verifies each claim and sends the result by email.

Where suppliers are based

32 suppliers in 9 countries

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Nafcillin price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Veterinary medication:.

Use classes: Pharmaceuticals.

Pharmacological actions

  • Anti-Bacterial Agents

Roles

  • antibacterial agent
  • antibacterial drug
  • antiinfective agent
  • antimicrobial agent
  • antimicrobial drug
  • pharmaceutical

Pharmacology

Nafcillin is a Penicillin-class Antibacterial.

How it is made

6-Aminopenicillanic acid is acylated by treatment with 2-ethoxy-1-naphthoyl chloride in anhydrous org solvent containing triethylamine. Aq extract of this...is admixed with water-immiscible solvent & nafcillin pptd by addn of sulfuric acid. Nafcillin sodium is pptd by mixing ethanolic solution of acid & sodium ethylhexanoate

Regulatory status

Inventories, regulations and trade controls that list this substance

Health and food

  • Active ingredient in FDA approved drug labels

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Nafcillin is traded under.

HS 2941.10Indicative HS code

Penicillins and their derivatives with a penicillanic acid structure, salts thereof

World exports in 2024
$1.66B
−2.5% vs 2023, imports $1.63B
2019 to 2024
Top exporters
  1. China56.8%
  2. Spain13.1%
  3. India * partner reported7.7%
Top importers
  1. India * partner reported16.4%
  2. Austria9.3%
  3. Brazil5.4%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Nafcillin is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Nafcillin, based on the data on this page

What is Nafcillin?

Nafcillin is a penicillin in which the substituent at position 6 of the penam ring is a (2-ethoxy-1-naphthoyl)amino group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a nafcillin(1-).

What is the CAS number of Nafcillin?

The CAS registry number of Nafcillin is 147-52-4. Other or deprecated CAS numbers: 985-16-0.

What is the molecular formula and weight of Nafcillin?

The molecular formula of Nafcillin is C21H22N2O5S and its molar mass is 414.48 g/mol.

What is Nafcillin used for?

Veterinary medication:. Use classes: Pharmaceuticals.

Is Nafcillin hazardous?

Nafcillin carries the GHS signal word "Danger". Main hazards: may cause an allergic skin reaction, may cause allergy or asthma symptoms or breathing difficulties if inhaled. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Nafcillin?

Nafcillin is usually classified under HS code 294110 (Penicillins and their derivatives with a penicillanic acid structure, salts thereof). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Nafcillin?

CompoundList lists 32 suppliers of Nafcillin in United States, China, Germany, Spain and 5 more. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

What is the price of Nafcillin?

Suppliers quote Nafcillin on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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