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Home> Encyclopedia >Pharmaceutical Intermediates>Antineoplastic Agents>Organic Intermediate
Lapatinib ditosylate structure
Lapatinib ditosylate structure

Lapatinib ditosylate

Iupac Name:N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine;4-methylbenzenesulfonic acid
CAS No.: 388082-78-8
Molecular Weight:925.46
Modify Date.: 2022-12-13 13:46
Introduction: Lapatinib is available in 250-mg tablets for oral administrationand is used in combination with cabecitabine in thetreatment of breast cancer for those patients that over expressthe type 2 EGF-R and who have previously receivedtaxane, anthracycline, and trastuzumab therapy. The type 2EGF-R is one subtype of this receptor and is also known asHER2 or ErbB-2. The agent is a receptor TK inhibitor targetingthe ErbB-1 and ErbB-2 subtypes. Binding occurs atthe ATP-binding site and thereby prevents phosphorylationand the subsequent activation of other kinase enzymes.ErbB-1 overexpression occurs in approximately27% to 30% of breast cancers, while ErbB-2 is over expressedin 20% to 25% of cases.The agent has demonstratedIC50 values of <0.2μM against ErbB-1 and 2 fromseveral different cancer cell lines and dissociates slowly(t1/2=300 min) from these receptor TKs.The drug isboth a substrate and an inhibitor of the efflux transportersPgp and BCRP. It is also an inhibitor of the hepatic uptaketransporter OATP1B1, which is an organic anion transporter.The absorption of lapatinib is incomplete andvariable after oral administration. The agent is extensivelymetabolized by CYP3A4 and CYP3A5, with minor contributionsfrom CYP2C19 and CYP2C8. Lapatinib inhibitsCYP3A and CYP2C8 at clinically relevant concentrations.The agent is highly (99%) protein bound and eliminatedprimarily in the feces. The half-life of the agent increaseupon repeated dosing, taking 6 days to reach steady statethat gives an effective half-life of 24 hours. The most commonlyseen adverse effects of lapatinib therapy are skinrash and diarrhea. Skin rash is commonly seen with manyof the other TK inhibitors and agents that target ErbB-1.Lapatinib-induced diarrhea is usually mild to moderate.There have been reports of decreases in left ventricularejection fraction associated with the agent, although thisappears to occur only rarely and is reversible upon discontinuationof therapy. Lapatinib ditosylateSupplier View more+
1. Names and Identifiers
1.1 Name
Lapatinib ditosylate
1.2 Synonyms

4-Quinazolinamine, N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[[[2-(methylsulfonyl)ethyl]amino]methyl]-2-furanyl]-, 4-methylbenzenesulfonate, hydrate (1:2:1) benzenesulfonic acid: N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6 -[5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine: h ydrate Lapatinib Ditosilate Lapatinib Ditosylate (GW-572016) Lapatinib ditosylate (USAN) Lapatinib ditosylate hydrate Lapatinib ditosylate monohydrate lapatinib(GW572016) Lapatinib, Tykerb, GW572016 N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine bis(4-methylbenzenesulfonate) N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[[[2-(methylsulfonyl)ethyl]amino]methyl]-2-furanyl]-4-quinazolinamine, 4-methylbenzenesulfonate, hydrate (1:2:1) N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine 4-methylbenzenesulfonate hydrate (1:2:1) N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furyl]quinazolin-4-amine bis(4-methylbenzenesulfonate) hydrate T66 BN DNJ EMR CG DO1R CF&& H- BT5OJ E1M2SW1 &&2 p-Tosoh H2O

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1.3 CAS No.
388082-78-8
1.4 CID
11557040
1.5 EINECS(EC#)
642-915-3
1.6 Molecular Formula
C41H40ClFN4O11S3 (isomer)
1.7 Inchi
InChI=1S/C29H26ClFN4O4S.2C7H8O3S.H2O/c1-40(36,37)12-11-32-16-22-9-10-27(39-22)24-14-21(35-29-23-7-2-3-8-26(23)33-18-34-29)15-25(30)28(24)38-17-19-5-4-6-20(31)13-19;2*1-6-2-4-7(5-3-6)11(8,9)10;/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35);2*2-5H,1H3,(H,8,9,10);1H2
1.8 InChIkey
UDGDJZMBLIHDBS-UHFFFAOYSA-N
1.9 Canonical Smiles
O.CC1=CC=C(C=C1)S(O)(=O)=O.CC1=CC=C(C=C1)S(O)(=O)=O.CS(=O)(=O)CCNCC1=CC=C(O1)C1=CC(NC2=NC=NC3=C2C=CC=C3)=CC(Cl)=C1OCC1=CC(F)=CC=C1
1.10 Isomers Smiles
CC1=CC=C(C=C1)S(=O)(=O)O.CC1=CC=C(C=C1)S(=O)(=O)O.CS(=O)(=O)CCNCC1=CC=C(O1)C2=CC3=C(C=C2)N=CN=C3NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl.O
2. Properties
2.1 Density
1.381
2.1 Melting point
>200oC (dec.)
2.1 Boiling point
750.7°C at 760 mmHg
2.1 Refractive index
n20/D 1.5520(lit.)
2.1 Flash Point
407.8°C
2.1 Precise Quality
924.17400
2.1 PSA
240.23000
2.1 logP
12.32880
2.1 Appearance
colourless to light-yellow crystal
2.2 StorageTemp
under inert gas (nitrogen or Argon) at 2-8°C
3. Use and Manufacturing
3.1 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 4 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H360 (50%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H362 (25%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
H372 (25%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]
H373 (25%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H413 (75%): May cause long lasting harmful effects to aquatic life [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, P281, P308+P313, P314, P405, and P501
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3.2 Usage
anticancer
4. Safety and Handling
4.1 Hazard Codes
Xi,N
4.1 Risk Statements
S24-S37-S61
4.1 Safety Statements
R43:May cause sensitization by skin contact. R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

H413 May cause long lasting harmful effects to aquatic life

Precautionary statement(s)
Prevention

P273 Avoid release to the environment.

Response

none

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Uses
anticancer
9.1 Uses
binds to a(1), dopamine, histamine H1, muscarinic, and serotonin type 2 (5-HT2) receptors atypical antipsychotic agent
9.2 Target
Value
9.3 ErbB2 (Cell-free assay)
9.2 nM
9.4 EGFR (Cell-free assay)
10.8 nM
9.5 ErbB4 (Cell-free assay)
367 nM
9.6 Uses
Lapatinib ditosylate monohydrate is a form of Lapatinib I, an orally active drug for breast cancer as a dual EGFR and erbB-?2 inhibitor.
9.7 General Description
Lapatinib is available in 250-mg tablets for oral administrationand is used in combination with cabecitabine in thetreatment of breast cancer for those patients that over expressthe type 2 EGF-R and who have previously receivedtaxane, anthracycline, and trastuzumab therapy. The type 2EGF-R is one subtype of this receptor and is also known asHER2 or ErbB-2. The agent is a receptor TK inhibitor targetingthe ErbB-1 and ErbB-2 subtypes. Binding occurs atthe ATP-binding site and thereby prevents phosphorylationand the subsequent activation of other kinase enzymes.ErbB-1 overexpression occurs in approximately27% to 30% of breast cancers, while ErbB-2 is over expressedin 20% to 25% of cases.The agent has demonstratedIC50 values of <0.2μM against ErbB-1 and 2 fromseveral different cancer cell lines and dissociates slowly(t1/2=300 min) from these receptor TKs.The drug isboth a substrate and an inhibitor of the efflux transportersPgp and BCRP. It is also an inhibitor of the hepatic uptaketransporter OATP1B1, which is an organic anion transporter.The absorption of lapatinib is incomplete andvariable after oral administration. The agent is extensivelymetabolized by CYP3A4 and CYP3A5, with minor contributionsfrom CYP2C19 and CYP2C8. Lapatinib inhibitsCYP3A and CYP2C8 at clinically relevant concentrations.The agent is highly (99%) protein bound and eliminatedprimarily in the feces. The half-life of the agent increaseupon repeated dosing, taking 6 days to reach steady statethat gives an effective half-life of 24 hours. The most commonlyseen adverse effects of lapatinib therapy are skinrash and diarrhea. Skin rash is commonly seen with manyof the other TK inhibitors and agents that target ErbB-1.Lapatinib-induced diarrhea is usually mild to moderate.There have been reports of decreases in left ventricularejection fraction associated with the agent, although thisappears to occur only rarely and is reversible upon discontinuationof therapy.
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10. Computational chemical data
  • Molecular Weight: 925.46g/mol
  • Molecular Formula: C41H40ClFN4O11S3
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 942.1841276
  • Monoisotopic Mass: 942.1841276
  • Complexity: 1100
  • Rotatable Bond Count: 13
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 16
  • Topological Polar Surface Area: 241
  • Heavy Atom Count: 63
  • 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: 4
  • CACTVS Substructure Key Fingerprint: AAADcfB/vQBkAAAAAAAAAAAAAAAAASAAAAA8YMGDAAAAAACx/AAAHwYQCAAADA7l3i639/bIFMqoA6ZzZHDCiGk1J/AJ2Lm+b9iOLvPF//uHPSjs0BPY6ae42fOeGEACAAICCAAwgAQABAQQAAAAAAAAAA==
11. Question & Answer
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13. Realated Product Infomation