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Oncology and immunology drugs

Gemcitabine

Also known as 2'-Deoxy-2',2'-difluorocytidine, 2',2'-Difluorodeoxycytidine, dFdC

CAS 95058-81-4Formula C9H11F2N3O4Molar mass 263.20 g/molEC 619-100-6
GHS signal word: Danger. Pictograms: Harmful or irritant, Serious health hazard, Hazardous to the environment 119 suppliers listed Drug substance
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Gemcitabine chemical structure, C9H11F2N3O4, CAS 95058-81-4
2D chemical structure

Key facts

What buyers check first

All properties
CAS number
95058-81-4
Formula
C9H11F2N3O4
Molar mass
263.20 g/mol
Appearance
Crystals from water, pH = 8.5
HS code
293499
Category
Oncology and immunology drugs
Illustrative photo, a shrink wrapped pallet of kraft paper sacks in a chemical plant
Typical packagingIllustrative packaging image, not the actual product

What is Gemcitabine?

Plain description, key identifiers and synonyms

Gemcitabine is a 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. It has a role as a radiosensitizing agent, an antimetabolite, an antineoplastic agent, a xenobiotic, an immunosuppressive agent, an antiviral drug, a photosensitizing agent, a prodrug, a DNA synthesis inhibitor, an EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor and an environmental contaminant. It is a pyrimidine 2'-deoxyribonucleoside and an organofluorine compound.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
CAS number
95058-81-4 CAS number cross-checkedOther or deprecated CAS: 103882-84-4
EC number
619-100-6
Molecular formula
C9H11F2N3O4
UNII
B76N6SBZ8R
MDL number
MFCD00869720
InChIKey
SDUQYLNIPVEERB-QPPQHZFASA-N
InChI
InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
Canonical SMILES
Nc1ccn(C2OC(CO)C(O)C2(F)F)c(=O)n1
Isomeric SMILES
C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F

Synonyms

  • 2'-Deoxy-2',2'-difluorocytidine
  • 2',2'-Difluorodeoxycytidine
  • dFdC
  • Gemcitabina
  • Gemcitabinum
  • DFdCyd
  • 4-Amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
  • 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
  • 2',2'-difluoro-2'-deoxycytidine
  • 2'deoxy-2',2'-difluorocytidine
  • 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
  • gemicitabine
  • 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydropyrimidin-2-one
  • 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidin-2-one
  • Hydrochloride, Gemcitabine
  • 2'-deoxy-2'-difluorocytidine
  • 2' Deoxy 2' Difluorocytidine
  • 1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose
  • 188011, LY
  • 2' Deoxy 2',2'' Difluorocytidine 5' O Monophosphate
  • 2',2'-DFDC
  • Difluorodeoxycytidine
  • Cytidine, 2'-deoxy-2',2'-difluoro-
  • Gemcitabine free base
  • 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
Show all 36 synonyms
  • Gamcitabine
  • LY 188011
  • Folfugem
  • Gemcel
  • Zefei
  • GemLip
  • 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
  • Gemzar (hydrochloride)
  • 95058-81-4 (free base)
  • Gemcitabine (USAN/INN)
  • Gecitabine base

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

Appearance
Crystals from water, pH = 8.5exp.

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
263.20 g/molcalc.
Exact mass
263.0718 Dacalc.
LogP (octanol/water)
-1.29calc.
Topological polar surface area
110.6 Ųcalc.
Hydrogen bond donors
3calc.
Hydrogen bond acceptors
6calc.
Rotatable bonds
2calc.
Heavy atoms
18calc.
Rings
2calc.
Aromatic rings
1calc.
Fraction sp3 carbons
0.56calc.
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=c1ncccn1C1CCCO1

O=c1ncccn1C1CCCO1

2 rings, 12 atoms.

1,589 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
GHS09: Hazardous to the environment
Hazardous to the environment

Hazard statements

  • H302Harmful if swallowed.
  • H312Harmful in contact with skin.
  • H315Causes skin irritation.
  • H319Causes serious eye irritation.
  • H335May cause respiratory irritation.
  • H340May cause genetic defects.
  • H351Suspected of causing cancer.
  • H360May damage fertility or the unborn child.
  • H360FDMay damage fertility. May damage the unborn child.
  • H361Suspected of damaging fertility or the unborn child.
  • H361fdSuspected of damaging fertility. Suspected of damaging the unborn child.
  • H372Causes damage to organs through prolonged or repeated exposure.

2 more on the safety page.

Precautionary statements (25)
  • P203Obtain, read and follow all safety instructions before use.
  • P260Do not breathe dust, fume, gas, mist, vapours or spray.
  • P261Avoid breathing dust, fume, gas, mist, vapours or spray.
  • P264Wash skin thoroughly after handling.
  • P264 + P265Wash skin thoroughly after handling. Do not touch eyes.
  • P270Do not eat, drink or smoke when using this product.
  • P271Use only outdoors or in a well-ventilated area.
  • P273Avoid release to the environment.
  • P280Wear protective gloves, protective clothing, eye protection and face protection.
  • P301 + P317If swallowed: Get medical help.
  • P302 + P352If on skin: Wash with plenty of water.
  • P304 + P340If inhaled: Remove person to fresh air and keep comfortable for breathing.
  • P305 + P351 + P338If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
  • P317Get medical help.
  • P318If exposed or concerned, get medical advice.
  • P319Get medical help if you feel unwell.
  • P321Specific treatment (see supplemental first aid instructions on the label).
  • P330Rinse mouth.
  • P332 + P317If skin irritation occurs: Get medical help.
  • P337 + P317If eye irritation persists: Get medical help.
  • P362 + P364Take off contaminated clothing. And wash it before reuse.
  • P391Collect spillage.
  • P403 + P233Store in a well-ventilated place. Keep container tightly closed.
  • P405Store locked up.
  • 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

Gemcitabine suppliers

Sponsored listings first, then the documented ranking: membership, verification, replies, completeness, freshness and ratings

All 119 suppliers
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Where suppliers are based

119 suppliers in 24 countries

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Gemcitabine 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

For use in combination with cisplatin for the first-line treatment of patients with inoperable, locally advanced (Stage IIIA or IIIB) or metastatic (Stage IV) non-small cell lung cancer.

In the treatment of ovarian cancer (Hydrochloride).

Therapeutic category: Antineoplastic.

Use classes: Antineoplastic and immunomodulating agents.

Pharmacological actions

  • Antimetabolites, Antineoplastic

Roles

  • DNA synthesis inhibitor
  • antiinfective agent
  • antimetabolite
  • antimicrobial agent
  • antimicrobial drug
  • antineoplastic agent
  • antiviral agent
  • antiviral drug
  • anxiolytic drug
  • central nervous system depressant
  • central nervous system drug
  • environmental contaminant
  • enzyme inhibitor
  • immunomodulator
  • immunosuppressive agent
  • pathway inhibitor
  • pharmaceutical
  • photosensitizing agent
  • pro-agent
  • prodrug
  • psychotropic drug
  • radiosensitizing agent
  • tranquilizing drug
  • xenobiotic

Pharmacology

Gemcitabine is a Nucleoside Metabolic Inhibitor. The mechanism of action of gemcitabine is as a Nucleic Acid Synthesis Inhibitor.

How it is made

Preparation: L.W. Hertel, GB 2136425, idem, US 4808614 (1984, 1989 both to Lilly)

The acetonide of 2,3-dihydroxypropanal (chiron- from mannitol) undergoes a Reformatsky reaction with ethyl 2,2-dibromo-2-fluoroacetate to yield the classic alcohol product, which is then benzylated to protect the generated OH group. Treatment with acid removes the acetonide group and the resulting diol forms a lactone with the gamma-OH function.

Read more

The free OH is benzylated (protection) and the lactone carbonyl reduced to form a mixture of isomers of 3,3-difluoro-4,5-di(benzyloxy)-2-furanol and the free OH is converted to a mesyl ester (I) with methanesulfonyl chloride and base. Cysteine is reacted with trimethylsilyl chloride to silylate the hydroxyl and amino groups (II). Compound I reacts with II, accompanied by loss of the mesyl group and, after removal of the benzyloxy groups with ammonia, yields the title compound.

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 Gemcitabine is traded under.

HS 2934.99Indicative HS code

Nucleic acids and their salts, other heterocyclic compounds, not elsewhere classified in heading 2934

World exports in 2024
$26.7B
+15.0% vs 2023, imports $26.3B
2019 to 2024
Top exporters
  1. Ireland26.3%
  2. China15.7%
  3. Singapore10.3%
Top importers
  1. United States24.5%
  2. Germany23.1%
  3. Japan4.5%
Reported customs values in USD, not prices.Full trade data

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

Frequently asked questions

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

What is Gemcitabine?

Gemcitabine is a 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.

What is the CAS number of Gemcitabine?

The CAS registry number of Gemcitabine is 95058-81-4. Other or deprecated CAS numbers: 103882-84-4.

What is the molecular formula and weight of Gemcitabine?

The molecular formula of Gemcitabine is C9H11F2N3O4 and its molar mass is 263.20 g/mol.

What is Gemcitabine used for?

For use in combination with cisplatin for the first-line treatment of patients with inoperable, locally advanced (Stage IIIA or IIIB) or metastatic (Stage IV) non-small cell lung cancer. In the treatment of ovarian cancer (Hydrochloride). Therapeutic category: Antineoplastic.

Is Gemcitabine hazardous?

Gemcitabine carries the GHS signal word "Danger". Main hazards: harmful if swallowed, harmful in contact with skin, causes skin irritation. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Gemcitabine?

Gemcitabine is usually classified under HS code 293499 (Nucleic acids and their salts, whether or not chemically defined, other heterocyclic…). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Gemcitabine?

CompoundList lists 119 suppliers of Gemcitabine in China, United States, India, Germany and 20 more. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

Where can I buy Gemcitabine in India?

17 suppliers in India list Gemcitabine on CompoundList. Filter the suppliers list by country and send a request to compare prices, grades and delivery times.

What is the price of Gemcitabine?

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

Guides for buyers

Practical guides that help when you source, ship or handle Gemcitabine

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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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