ChemicalBook > CAS DataBase List > 10-Hydroxycamptothecin

10-Hydroxycamptothecin

Product Name
10-Hydroxycamptothecin
CAS No.
19685-09-7
Chemical Name
10-Hydroxycamptothecin
Synonyms
SN38;HCPT;HYDROXYCAMPTOTHECIN;10-HCPT;(S)-10-HYDROXYCAMPTOTHECIN;Ampule;NSC 107124;HYDROCAMPTOTHECINE;hydroxy-camptotheci;Irinotecan USP RC A
CBNumber
CB4445430
Molecular Formula
C20H16N2O5
Formula Weight
364.35
MOL File
19685-09-7.mol
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10-Hydroxycamptothecin Property

Melting point:
265-270°C
Boiling point:
820.7±65.0 °C(Predicted)
Density 
1.60
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
≥23.8 mg/mL in DMSO with gentle warming; insoluble in EtOH; insoluble in H2O
pka
8.93±0.40(Predicted)
form 
powder to crystal
color 
White to Yellow to Orange
InChIKey
HAWSQZCWOQZXHI-FQEVSTJZSA-N
CAS DataBase Reference
19685-09-7(CAS DataBase Reference)
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Safety

Safety Statements 
24/25
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H340May cause genetic defects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2491
Product name
Irinotecan Related Compound A
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
25MG
Price
$485
Updated
2024/03/01
Sigma-Aldrich
Product number
1347610
Product name
Irinotecan Related Compound A
Packaging
10mg
Price
$1490
Updated
2024/03/01
TCI Chemical
Product number
H1463
Product name
10-Hydroxycamptothecin
Purity
>98.0%(HPLC)
Packaging
1g
Price
$231
Updated
2024/03/01
Cayman Chemical
Product number
14635
Product name
(S)-10-hydroxy-Camptothecin
Purity
≥98%
Packaging
25mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
14635
Product name
(S)-10-hydroxy-Camptothecin
Purity
≥98%
Packaging
50mg
Price
$107
Updated
2024/03/01
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10-Hydroxycamptothecin Chemical Properties,Usage,Production

Description

DNA topoisomerases relax supercoiled DNA during replication, transcription, recombination, repair, and chromosome condensation. The relaxation of DNA supercoiling by topoisomerase I at single-strand breaks represents a target for anticancer agents to intercalate between DNA base pairs, leading to the activation of apoptotic and cell cycle arrest pathways. (S)-10-hydroxy-Camptothecin is an inhibitor of topoisomerase I originally isolated from the Chinese tree C. acuminata. It is a member of the camptothecin family that demonstrates less toxicity than its parent compound. (S)-10-hydroxy-Camptothecin has strong anti-tumor activity against a wide range of experimental tumors including L1210 leukemia cells (IC50 = 1.15 μM). In vitro treatment of human HepG2 cells with 5-20 μM (S)-10-hydroxy-camptothecin results in cell cycle arrest at the G2/M phase.

Chemical Properties

Yellow Solid

Uses

A Camptothecin derivative; a topoisomerase inhibitor for cancer therapy

Definition

ChEBI: 10-Hydroxycamptothecin is a pyranoindolizinoquinoline.

in vitro

10-Hydroxycamptothecin inhibited the growth of BT-20 and MDA-231 cells with IC50 of 34.3nM and 7.27nM, respectively, which was more potent than camptothecin (CPT) with IC50>500nM. 10-Hydroxycamptothecin potently induces the formation of the pBR322 plasmid DNA cleavage complex mediated by human topoisomerase I with an EC50 of 0.35 μM, more than 50-fold more potent than CPT with an EC50 of 18.85 μM. 10-Hydroxycamptothecin treatment caused dose-dependent growth inhibition of human microvascular endothelial cells (HMECs) with IC50 of 0.31 μM and significantly inhibited HMEC migration with IC50 of 0.63 μM. Treatment of HMEC cells with 10-Hydroxycamptothecin also inhibited microtubule formation in a dose-dependent manner with IC50 of 0.96 μM. 10-Hydroxycamptothecin (5-20 nM) significantly inhibits the differentiation of Colo205 cells, arrests the cell cycle in G2 phase, and induces apoptosis through a caspase-3-dependent pathway.

in vivo

In the CAM model, 10-Hydroxycamptothecin treatment inhibited angiogenesis in a concentration-dependent manner, with 95% inhibition at 25 nM, more potent than suramin, which inhibited only 60% of angiogenesis at 125 nM. 10-Hydroxycamptothecin, administered orally at low doses of 2.5-7.5 mg/kg every two days, caused significant growth inhibition in Colo205 xenograft mice, but no acute toxicity. LD50: 104 mg/kg in mice (intraperitoneal injection).

IC 50

0.31 μm

References

[1] vladu b, woynarowski jm, manikumar g, wani mc, wall me, von hoff dd, wadkins rm. 7- and 10-substituted camptothecins: dependence of topoisomerase i-dna cleavable complex formation and stability on the 7- and 10-substituents. mol pharmacol. 2000 feb;57(2):243-51.
[2] xiao d, tan w, li m, ding j. antiangiogenic potential of 10-hydroxycamptothecin. life sci. 2001 aug 24;69(14):1619-28.
[3] ping yh, lee hc, lee jy, wu ph, ho lk, chi cw, lu mf, wang jj. anticancer effects of low-dose 10-hydroxycamptothecin in human colon cancer. oncol rep. 2006 may;15(5):1273-9.

10-Hydroxycamptothecin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 10-Hydroxycamptothecin manufacturers

Shanghai Standard Technology Co., Ltd.
Product
10-Hydroxycamptothecin 19685-09-7
Price
US $0.00/mg
Min. Order
5mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2019-11-20
Changzhou Rokechem Technology Co., Ltd.
Product
10-Hydroxycamptothecin 19685-09-7
Price
US $0.00-0.00/g
Min. Order
1g
Purity
≥98%
Supply Ability
1-10000g
Release date
2022-11-22
NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
10-Hydroxycamptothecin 19685-09-7 19685-09-7
Price
US $15.60/mg
Min. Order
20mg
Purity
98.00
Supply Ability
1000.00 kgs
Release date
2019-07-09

19685-09-7, 10-HydroxycamptothecinRelated Search:

10-HYDROXYCAMPTOTHECIN 10-Nitrocamptothecin (+)-Camptothecin Irinotecan hydrochloride 7-Ethyl-10-hydroxycamptothecin SN-38 GLUCURONIDE sodium:(2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-(4-piperidin-1-ylpiperidine-1-carbonyl)oxy-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate Irinotecan 7,11-Diethyl-10-hydroxycaMptothecin Irinotecan Impurity 6 Irinotecan EP Impurity H 12-Hydroxy Irinotecan 7-Ethylcamptothecin Irinotecan EP Impurity K (Mixture of Diastereomers) Irinotecan IMpurity G Irinotecan Impurity 5 RPR 121056 GURKHSYORGJETM-MGDILKBHSA-N

  • Camptothecae Acuminatae extract
  • hydrate,(s)-dihydroxy
  • hydroxy-camptotheci
  • Hydroxycamptothencine
  • (20S)-10-HYDROXYCAMPTOTHECIN 98%
  • (20S)-10-Hydroxycamptothecin
  • HYDROCAMPTOTHECINE
  • CAMPTOTHECIN, 10-HYDROXY(SH)
  • HYDROXYCAMPTOTHECIN, 10-(P)
  • 10-hydroxycamptothecin (TECANS)
  • 10-HYDROCAMPTOTHECIN
  • Ampule
  • (4S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
  • NSC 107124
  • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4-ethyl-4,10-dihydroxy-, (4S)-
  • (4S)-4,9-Dihydroxy-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
  • (S)-10-HYDROXYCAMPTOTHECIN
  • SN38
  • 10-Hydroxycamptothecin, 98%, from Taxus chinensis (Pilg.) Rehder
  • 10-HCPT
  • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-, (4S)-
  • (S)-10-Hydroxycamptothecin (4S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
  • Irinotecan USP RC A
  • Irinotecan Impurity 12
  • CAMPTOTHECIN, 10-HYDROXY-
  • CAMPTOTHECIN, 10-HYDROXY-, CAMPTOTHECA ACUMINATA
  • HCPT
  • HYDROXYCAMPTOTHECIN
  • HYDROXYCAMPTOTHECIN, 10-
  • (20S)-10-HYDROXYCAMPTOTHECIN (20S)-7-ETHYL-10-HYDROXYCAMPTOTHECIN (S)-10-HYDROXYCAMPTOTHECIN
  • CaMptothecin IMpurity
  • CaMptothecin 10-Hydroxy IMpurity
  • 10-HydroxycaMptothecin, froM Taxus chinensis
  • Irinotecan EP Impurity B
  • 10-Hydroxycamptothecin 19685-09-7
  • (S)-4-ethyl-4,9-dihydroxy-1H-pyrano
  • 10-HYDROXY CAMPTOTHECIN (IRINOTECAN EP IMPURITY B)
  • Fructus Camptothecae
  • (s)-10-hydroxycamptothecinhydrate
  • 4’:6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione,4-ethyl-4,9-1h-pyrano(3
  • 4’:6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione,4-ethyl-4,9-dihydroxy-,hydrate,(s)-1h-pyrano(3
  • (4S)-4α-Ethyl-4,9-dihydroxy-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione
  • (4S)-9-Hydroxy-4-hydroxy-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
  • 10-Hydroxycamptothecin
  • 10-Hydroxycamptothecine
  • HYDROXYCAMPTOTHECIN, 10-(RG)
  • 10-hydroxycamptothecin,HCPT
  • (S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione
  • Irinotecan Related CoMpound A
  • (+/-)-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione
  • Irinotecan Related Compound A (10 mg) ((S)-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione)
  • 1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
  • 10-HydroxycaMptothecin, HydroxycaMptothecine
  • Hydroxycamptothecin 80-98%
  • (S)-10-Hydroxycamptothecin,>98%
  • (20S)-10-Hydroxycamptothecine
  • Camptotheca acuminata fruit extract
  • (19S)-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione