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Dasatinib monohydrate structure
Dasatinib monohydrate structure

Dasatinib monohydrate

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 hydrate
CAS No.: 863127-77-9
Molecular Weight:506.02082
Modify Date.: 2022-11-23 18:48
Introduction:

ChEBI: A hydrate that is the monohydrate of dasatinib. It is used for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhyd ous dasatinib (INN).


Dasatinib monohydrate is a hydrate that is the monohydrate of dasatinib. It is used for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhydrous dasatinib (INN). It has a role as an antineoplastic agent and a tyrosine kinase inhibitor. It contains a dasatinib (anhydrous).|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.|Dasatinib is an orally bioavailable synthetic small molecule-inhibitor of SRC-family protein-tyrosine kinases. Dasatinib binds to and inhibits the growth-promoting activities of these kinases. Apparently because of its less stringent binding affinity for the BCR-ABL kinase, dasatinib has been shown to overcome the resistance to imatinib of chronic myeloid leukemia (CML) cells harboring BCR-ABL kinase domain point mutations. SRC-family protein-tyrosine kinases interact with a variety of cell-surface receptors and participate in intracellular signal transduction pathways; tumorigenic forms can occur through altered regulation or expression of the endogenous protein and by way of virally-encoded kinase genes.|A pyrimidine and thiazole derived ANTINEOPLASTIC AGENT and PROTEIN KINASE INHIBITOR of BCR-ABL KINASE. It is used in the treatment of patients with CHRONIC MYELOID LEUKEMIA who are resistant or intolerant to IMATINIB.

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1. Names and Identifiers
1.1 Name
Dasatinib monohydrate
1.2 Synonyms

5-Thiazolecarboxamide, N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-, hydrate (1:1) BMS-354825 Monohydrate cc-335 Dasatinib Dasatinib hydrate Dasatinib hydrate (JAN) Dasatinib monohydrate N-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide monohydrate Dasatinib R dasatinib.H2O Dasatinibmonohydrate MFCD08704581 N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)-1-piperazinyl)-2-methyl-4-pyrimidinyl)amino)-1,3-thiazole-5-carboxamide monohydrate N-(2-Chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl}amino)-1,3-thiazole-5-carboxamide hydrate (1:1) N-(2-Chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide hydrate (1:1) N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide hydrate N-(2-chloro-6-methylphenyl)-2-(6-(4-(3-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino) thiazole-5-carboxamide monohydrate n-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2- N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide monohydrate SPRYCEL (TN) UNII-RBZ1571X5H

1.3 CAS No.
863127-77-9
1.4 CID
11540687
1.5 EINECS(EC#)
638-874-6
1.6 Molecular Formula
C22H28ClN7O3S (isomer)
1.7 Inchi
InChI=1S/C22H26ClN7O2S.H2O/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31;/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27);1H2
1.8 InChkey
XHXFZZNHDVTMLI-UHFFFAOYSA-N
1.9 Canonical Smiles
CC1=C(C(=CC=C1)Cl)NC(=O)C2=CN=C(S2)NC3=CC(=NC(=N3)C)N4CCN(CC4)CCO.O
1.10 Isomers Smiles
CC1=C(C(=CC=C1)Cl)NC(=O)C2=CN=C(S2)NC3=CC(=NC(=N3)C)N4CCN(CC4)CCO.O
2. Properties
2.1 Density
1.408
2.1 Melting point
97-99?°C(lit.)
2.1 Precise Quality
505.16600
2.1 PSA
143.98000
2.1 logP
3.39810
2.1 Color/Form
Powder
2.2 Water Solubility
MAY DECOMPOSE
2.3 StorageTemp
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A hydrate that is the monohydrate of dasatinib. It is used for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhydous dasatinib (INN).
3.2 Usage
antineoplastic
4. Safety and Handling
4.1 Hazard Codes
C; Xi
4.1 Risk Statements
S26-S27-S28-S36/37/39-S45
4.1 Safety Statements
R34:Causes burns. R36/37/38:Irritating to eyes, respiratory system and skin .
4.1 Packing Group
II
4.1 Hazard Class
4.3
4.1 Hazard Declaration
H300
4.1 RIDADR
UN 3263 8/PG 2
4.1 Caution Statement
P201, P202, P260, P263, P264, P270, P273, P281, P301+P310, P308+P313, P309+P311, P314, P321, P330, P391, P405, P501
4.1 WGK Germany
3
4.1 RTECS
QD8530000
4.1 Specification

?Dasatinib ,?its cas register number is?863127-77-9.?It is also known as N-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide monohydrate .

4.2 Toxicity

?Neutropenia and myelosuppression were common toxic effects. Fifteen patients in the above-mentioned study developed pleural effusions, which were felt to be a side effect of dasatinib. Some of these patients required thoracentesis or pleurodesis to treat the effusions. Other adverse events included mild to moderate diarrhea, peripheral edema, and headache. A small number of patients developed abnormal liver function tests which returned to normal without dose adjustments. Mild hypocalcemia was also noted, but did not appear to cause any significant problems.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 2

Reproductive toxicity, Category 1B

Specific target organ toxicity \u2013 repeated exposure, Category 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H300 Fatal if swallowed

H360 May damage fertility or the unborn child

H361 Suspected of damaging fertility or the unborn child

H372 Causes damage to organs through prolonged or repeated exposure

H410 Very toxic to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

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.

P273 Avoid release to the environment.

Response

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.

P314 Get medical advice/attention if you feel unwell.

P391 Collect spillage.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Precursor and Product
8. Other Information
8.0 Target
Value
8.1 Abl (Cell-free assay)
0.6 nM
8.2 c-Kit (D816V) (Cell-free assay)
37 nM
8.3 c-Kit (wt) (Cell-free assay)
79 nM
8.4 Uses
antineoplastic
8.5 Uses
Dasatinib Monohydrate is an orally bioavailable synthetic small molecule-inhibitor of SRC-family protein-tyrosine kinases. It is a COVID19-related research product.
8.6 Definition
ChEBI: A hydrate that is the monohydrate of dasatinib. It is used for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhyd ous dasatinib (INN).
8.7 Brand name
Sprycel (Bristol-Myers Squibb).
8.8 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.
8.9 Drug Classes
Antineoplastic Agents
8.10 Mesh
Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)
8.11 Mesh Entry Terms
(18F)-N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide
9. Computational chemical data
  • Molecular Weight: 506.02082g/mol
  • Molecular Formula: C22H28ClN7O3S
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 505.1662866
  • Monoisotopic Mass: 505.1662866
  • Complexity: 642
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 10
  • Topological Polar Surface Area: 136
  • Heavy Atom Count: 34
  • 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: 2
  • CACTVS Substructure Key Fingerprint: AAADceB7sABEAAAAAAAAAAAAAAAAAWAAAAA8WIAAAAAAAAAB8AAAHgYQCAAADArh2yY/8ZfIEgisAjd3dACC8Kl1D7lJ2C04ZtiKeCrB29HUJIholALYyOcQgAAOAAAAIAACABAAAABAAAQAIAAAAAAAAA==
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