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Home> Encyclopedia >Pharmaceutical>Pharmaceutical Intermediates>Organic Intermediate
Dasatinib structure
Dasatinib structure


Iupac Name:N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-1,3-thiazole-5-carboxamide
CAS No.: 302962-49-8
Molecular Weight:488.007
Modify Date.: 2022-11-23 18:48
Introduction: Dasatinib, developed and marketed by Bristol Myers, isthe first approved oral tyrosine kinase inhibitor which bindsto multiple conformations of ABL kinase for the treatment oftwo leukemia indications: chronic myeloid leukemia (CML)and Philadelphia chromosome-positive acute lymphoblasticleukemia (Ph+ ALL). Dasatinib is a highly potent, ATPcompetitive ATPcompetitivekinase inhibitor which, at nanomolar concentrations,inhibits BCR-ABL, SRC family, c-KIT, EPHA2 andPDGFR-B. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

25MG/100MG/1G 5-Thiazolecarboxamide, N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]- BMS 345825 BMS 354825 BMS 35482513 BMS354825 BMS-354825 CS-1968 DASATINIB (BMS 354825) Dasatinib (Dasatinib Monohydrate) Tablet KIN 001-5 N-(2-chloro-6-Methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-Methyl-4-pyriMidinyl]aMino]-1,3-thiazole-5-carboxaMide N-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide NCGC00181129 NSC 759877 SPRYCEL sprycel Dasatinib Spyrcel

View all
1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C22H26ClN7O2S (isomer)
1.7 Inchi
1.8 InChIkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
2.1 Refractive index
2.1 Flash Point
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Appearance
2.2 Storage
-20°C Freezer
2.3 Chemical Properties
White solid
2.4 Color/Form
2.5 Physical
2.6 pKa
2.7 Water Solubility
1.28e-02 g/L
3. Use and Manufacturing
3.1 General Description
Dasatinib is available in 20-, 50-, and 70-mg tablets fororal administration in the treatment of CML and ALL thatare Ph1 positive. Although dasatinib is more potent thanimatinib, bioavailability is much lower with values rangingbetween 14% to 34%. The agent is extensively metabolizedwith as many as 29 metabolites seen as result of oxidationby primarily CYP3A4 and phase II conjugation.The agent may act as an inhibitor of CYP3A4 andCYP2C8. Metabolism does give an active metabolite, but this accounts for only 5% of the total and is not believed tobe important for the overall activity of the agent. Dasatinibis 95% protein bound with a terminal half-life of 3 to5 hours. The majority of the drug and metabolites are eliminatedin the feces. The most common side effects are skinrash, nausea, diarrhea, and fatigue. Serious side effects includemyelosuppression appearing as neutropenia andthrombocytopenia, bleeding of the brain and GI tract, andfluid retention.
3.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 10 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H301 (90%): Toxic if swallowed [Danger Acute toxicity, oral]
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
H318 (40%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H351 (50%): Suspected of causing cancer [Warning Carcinogenicity]
H360 (40%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H361 (60%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H362 (30%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
H371 (30%): May cause damage to organs [Warning Specific target organ toxicity, single exposure]
H372 (50%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]
H373 (40%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H410 (40%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P263, P264, P270, P273, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P309+P311, P310, P314, P321, P330, P332+P313, P362, P391, P405, and P501
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3.3 Usage
Suitable for treatment of chronic myeloid leukemia which is resistant or intolerant to the treating programs including imatinib mesylate.
4. Safety and Handling
4.1 Hazard Declaration
4.1 Caution Statement
P201, P202, P260, P263, P264, P270, P273, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P309+P311, P310, P314, P321, P330, P332+P313, P362, P391, P405, P501
4.1 WGK Germany

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Reproductive toxicity, Category 1B

Reproductive toxicity, Additional category for effects on or via lactation

Specific target organ toxicity \u2013 single exposure, Category 2

Specific target organ toxicity \u2013 repeated exposure, Category 2

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H301 Toxic if swallowed

H360 May damage fertility or the unborn child

H362 May cause harm to breast-fed children

H371 May cause damage to organs

H373 May cause damage to organs through prolonged or repeated exposure

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P263 Avoid contact during pregnancy and while nursing.


P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

P308+P311 IF exposed or concerned: Call a POISON CENTER/doctor/...

P314 Get medical advice/attention if you feel unwell.


P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


6. NMR Spectrum
7. Synthesis Route
9. Other Information
9.0 Livertox Summary
Dasatinib is a selective tyrosine kinase receptor inhibitor that is used in the therapy of chronic myelogenous leukemia (CML) positive for the Philadelphia chromosome. Dasatinib is commonly associated with transient elevations in serum aminotransferase levels during treatment, but with only rare instances of clinically apparent acute liver injury.
9.1 Drug Classes
Antineoplastic Agents
9.2 Mesh
Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)
9.3 Absorption
Dasatinib is extensively metabolized in humans, primarily by the cytochrome P450 enzyme 3A4. Elimination is primarily via the feces.|2505 L
9.4 Metabolism
Dasatinib is extensively metabolized in humans, primarily by the cytochrome P450 enzyme 3A4
9.5 Biological Half Life
The overall mean terminal half-life of dasatinib is 3-5 hours.
9.6 Mesh Entry Terms
9.7 Use Classification
Human drugs -> Sprycel -> EMA Drug Category|Antineoplastic agents -> Human pharmacotherapeutic group|Human drugs -> Rare disease (orphan)|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
10. Computational chemical data
  • Molecular Weight: 488.007g/mol
  • Molecular Formula: C22H26ClN7O2S
  • Compound Is Canonicalized: True
  • XLogP3-AA: 3.6
  • Exact Mass: 487.1557220
  • Monoisotopic Mass: 487.1557220
  • Complexity: 642
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 9
  • Topological Polar Surface Area: 135
  • Heavy Atom Count: 33
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
11. Question & Answer
  • Dasatinib, formerly known as BMS-354825, is a cancer treatment drug produced by Bristol-Myers Squibb and sold under the name "Sprycel". It is a tyrosine kinase inhibitor that targets the Philadelphia ..
  • Dasatinib is a medication that has proven to be effective in treating various diseases. However, it is important to note that its usage may vary for different age groups or individuals. So, what exact..
  • The relationship between medication and our lives is very close. Many consumers often take medication to improve sub-health symptoms and ensure their own health. Some consumers even go to the hospital..
  • Dasatinib (brand name Sprycel) is an orally administered tyrosine kinase inhibitor developed by Bristol-Myers Squibb. It was approved by the US FDA on June 28, 2006, for the treatment of all phases of..
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