Imatinib

Iupac Name：4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide

Molecular Weight：493.615

Introduction: Imatinib is a kind of oral drugs used for the treatment of the chronic myelogenous leukemia (abbreviated CML) of positive symptoms of Philadelphia chromosome (Ber-Abl). It is suitable for being applied to adult patients in acute transformation phase, accelerated phase, and chronic phase with treatment failure with interferon. CML is a kind of hematopoietic stem cell disease caused by the DNA abnormalities in the bone marrow stem cells. DNA abnormalities will produce abnormal proteins and interfere with the normal generation process of the white blood cells in the bone marrow, resulting in the sharp increase in the number of white blood cells. CML is divided into three phases including chronic phase, accelerated phase and crisis phase with the average survival period of the patients in crisis phase being only 2-3 months. Imatinib is also effective in treating the gastrointestinal stromal tumor with the efficiency being about 50%. View more+

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1. Names and Identifiers

1.1 Name: Imatinib
1.2 Synonyms: 1iep 1xbb 4-(4-Methyl-piperazin-1-ylMethyl)-N-[4-Methyl-3-(4-pyridin-3-yl-pyriMidin-2-ylaM 4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE 4-[(4-Methyl-1-piperazinyl)methyl]-N-(4-methyl-3-{[4-(3-pyridinyl)-2-pyrimidinyl]amino}phenyl)benzamide 4-[(4-methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide 4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide Benzamide, 4-((4-methyl)-1-piperazinyl)methyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)- Benzamide, 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]- Benzamide, 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]- (9CI) Imantinib base Imatinib (4-[(4-Methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide Imatinib (STI571) Imatinib free base IMatinib(STI571) IMatinib-D4 MFCD05662257 STI571 UNII-BKJ8M8G5HI Veenat

1.3 CAS No.: 152459-95-5

1.4 CID: 5291

1.5 EINECS(EC#): 604-855-6

1.6 Molecular Formula: C29H31N7O (isomer)

1.7 Inchi: InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)

1.8 InChkey: KTUFNOKKBVMGRW-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5

1.10 Isomers Smiles: CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5

2. Properties

3.1 Density: 1.255

3.1 Melting point: 208-210°C (dec.)

3.1 Boiling point: 754.9°C at 760 mmHg

3.1 Refractive index: 1.67

3.1 Flash Point: 410.3°C

3.1 Vapour pressure: 6.03E-24mmHg at 25°C

3.1 Precise Quality: 493.25900

3.1 PSA: 86.28000

3.1 logP: 4.61210

3.1 Appearance: off white powder

3.2 Chemical Properties: Orange Solid

3.3 Color/Form: Powder

3.4 Physical: Solid

3.5 pKa: pKa1 8.07; pKa2 3.73; pKa3 2.56; pKa4 1.52(at 25℃)

3.6 StorageTemp: Keep in dark place,Sealed in dry,Store in freezer, under -20°C

3. Use and Manufacturing

4.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 5 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (20%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H341 (40%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
H351 (60%): Suspected of causing cancer [Warning Carcinogenicity]
H360 (40%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H361 (40%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H362 (40%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
H373 (20%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H411 (20%): Toxic to aquatic life with long lasting effects [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+P312, P302+P352, P305+P351+P338, P308+P313, P314, P321, P330, P332+P313, P337+P313, P362, P391, P405, and P501

4.2 Usage: Imatinib can be used for the treatment of the chronic myelogenous leukemia (abbreviated CML) of positive symptoms of Philadelphia chromosome (Ber-Abl). It is suitable for being applied to adult patients in acute transformation phase, accelerated phase, and chronic phase with treatment failure with interferon.

4. Safety and Handling

5.1 Hazard Codes: T; N

5.1 Risk Statements: S28-S36/37-S45-S61-S24/25-S23-S53

5.1 Safety Statements: 24/25

5.1 Packing Group: II

5.1 Hazard Class: 6.1

5.1 RIDADR: UN 1662 6.1/PG 2

5.1 WGK Germany: 3

5.1 RTECS: CV5585673

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

152459-95-5Total: 38 Synthesis Route

99-55-8 195 Suppliers

152459-95-5 329 Suppliers

Literatures:
Journal of Medicinal Chemistry, , vol. 48, # 1 p. 249 - 255
Yield: null

99-99-0 58 Suppliers

152459-95-5 329 Suppliers

Literatures:
Organic Process Research and Development, , vol. 12, # 3 p. 490 - 495
Yield: null

104-85-8 108 Suppliers

152459-95-5 329 Suppliers

Literatures:
Organic Process Research and Development, , vol. 16, # 11 p. 1794 - 1804
Yield: null

View all

7. Precursor and Product

precursor:

152460-07-6

99-55-8

571187-03-6

109-01-3

1692-25-7

404844-11-7

1642-81-5

66521-66-2

3006-96-0

99-99-0

7745-93-9

152460-10-1

7745-91-7

1025717-41-2

350-03-8

874-86-2

104-85-8

125743-63-7

55314-16-4

17201-43-3

314268-40-1

152460-09-8

View all

product :

571186-91-9

8. Other Information

8.0 Merck: 14,4902

8.1 Product description: Imatinib is a kind of oral drugs used for the treatment of the chronic myelogenous leukemia (abbreviated CML) of positive symptoms of Philadelphia chromosome (Ber-Abl). It is suitable for being applied to adult patients in acute transformation phase, accelerated phase, and chronic phase with treatment failure with interferon. CML is a kind of hematopoietic stem cell disease caused by the DNA abnormalities in the bone marrow stem cells. DNA abnormalities will produce abnormal proteins and interfere with the normal generation process of the white blood cells in the bone marrow, resulting in the sharp increase in the number of white blood cells. CML is divided into three phases including chronic phase, accelerated phase and crisis phase with the average survival period of the patients in crisis phase being only 2-3 months.
Imatinib is also effective in treating the gastrointestinal stromal tumor with the efficiency being about 50%.

8.2 Approved indications in Europe, the United States and other countries: Novartis's imatinib (imatinib, Glivec) had been approved in Switzerland for being used as first-line drug for the treatment of early-stage adult chronic myelogenous leukemia and can also be applied to patients with various types of chronic granulocytic leukemia. Switzerland is the first countries which had approved to additionally include the above two indications of this drug.
On July 28, 2006, the European Agency for the Evaluation of Medicinal Products (EMEA) had recommended the imatinib (Gleevec) of the Novartis Company for the treatment of two new indications-dermatofibrosarcoma protuberans (DFSP) and Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph + ALL). These final approvals of these two indications still need to wait the decision of the European Food and Drug Administration.
In addition, Novartis has announced that the application of imatinib in treating hypereosinophilic syndrome and systemic mastocytosis is still in the approval process of FDA and EMEA.
The drug has currently been approved in Europe, the United States and other countries for the treatment of Philadelphia chromosome-positive chronic myeloid leukemia (Ph + CML) and gastrointestinal stromal tumors.

8.3 Precautions: When combined with Ketoconazole, itraconazole, erythromycin, clarithromycin, the Cmax of this drug can (the maximum plasma concentration after the first drug administration) be increased by an average of 26% with the AUC being increased by 40%.
The inducers of the metabolizing enzyme of hepatic drugs such as dexamethasone, phenytoin, carbamazepine, rifampicin and barbiturates can significantly reduce blood concentration of the drug.
When the CYP3A4 metabolized substrates such as simvastatin, cyclosporine, pimozide, etc. were used in combined with imatinib, the plasma concentration of those drugs can be increased due to its competing with the drug enzyme.

8.4 Uses: Imatinib can be used for the treatment of the chronic myelogenous leukemia (abbreviated CML) of positive symptoms of Philadelphia chromosome (Ber-Abl). It is suitable for being applied to adult patients in acute transformation phase, accelerated phase, and chronic phase with treatment failure with interferon.

8.5 Chemical Properties: Orange Solid

8.6 Uses: antineoplastic

8.7 Uses: atypical antipsychotic

8.8 Uses: Imatinib impurity.

8.9 Target: Value

8.10 PDGFR (Cell-free assay): 100 nM

8.11 v-Abl (Cell-free assay): 600 nM

8.12 Uses: Imatinib Mesylate is orally bioavailability mesylate salt of Imatinib, which is a multi-target inhibitor of v-Abl, c-Kit and PDGFR with IC50 of 0.6 μM, 0.1 μM and 0.1 μM, respectively. Imatinib also known as Gleevec, Glivec, CGP-57148B, STI-571 & Imatinib

8.13 Indications: Imantinib mesylate (Gleevec) is a rationally designed inhibitor of the tumor-specific bcr-abl kinase. The Philadelphia chromosome, present in nearly all patients with chronic myelogenous leukemia (CML), is produced by a chromosomal rearrangement linking the bcr and the abl genes. The bcr-able kinase is therefore a unique drug target in leukemic cells, and imantinib selectively and potently inhibits this kinase. Remissions in CML patients are achieved with high frequency and very low toxicity, and this compound may become a front-line agent for treating this cancer. Unfortunately, drug resistance has already been observed in the clinic as a result of mutations in the bcr-abl kinase, and this magic bullet does not appear to be curative for CML patients. Extension of the use of imantinib to other tumor types with overexpression of c-kit kinase or platelet-derived growth factor kinase is undergoing development because of its observed activity against these kinases.

9. Computational chemical data

Molecular Weight：493.615g/mol
Molecular Formula：C₂₉H₃₁N₇O
Compound Is Canonicalized：True
XLogP3-AA：3.5
Exact Mass：493.25900864
Monoisotopic Mass：493.25900864
Complexity：706
Rotatable Bond Count：7
Hydrogen Bond Donor Count：2
Hydrogen Bond Acceptor Count：7
Topological Polar Surface Area：86.3
Heavy Atom Count：37
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

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