DC Chemicals Limited
China
Product Name: Valrubicin (AD-32)
Price: $600.0/100mg $1200.0/250mg $2500.0/1g
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

56124-62-0

56124-62-0 structure

56124-62-0 structure

Name: Valrubicin
Chemical Name: Valrubicin
CAS Number: 56124-62-0
Molecular Formula: C₃₄H₃₆F₃NO₁₃
Molecular Weight: 723.644
Catalog: API Antineoplastic agents Antibiotic antineoplastic agents
Create Date: 2018-07-06 10:35:10
Modify Date: 2024-01-02 20:39:46
Valrubicin is a chemotherapy agent, inhibits TPA- and PDBu-induced PKC activation with IC50s of 0.85 and 1.25 μM, respectively, and has antitumor and antiinflammatory activity.

Name	Valrubicin
Synonyms	2-Oxo-2-[(2S,4S)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-({2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-α-L-lyxo-hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydro-2-tetracenyl]ethyl valerate Valrubicin 2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-({2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-α-L-lyxo-hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate Vinorelbine (BICINS ) N-trifluoroacetyladriamycin-14-valerate Pentanoic acid, 2-[(2S,4S)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-[[2,3,6-trideoxy-3-[(2,2,2-trifluoroacetyl)amino]-α-L-lyxo-hexopyranosyl]oxy]-2-naphthacenyl]-2-oxoethyl ester trifluoroacetyl-adriamyci14-valerate N-(trifluoroacetyl)adriamycin 14-valerate (AD 32) 2-Oxo-2-[(2S,4S)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-({2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-α-L-lyxo-hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl valerate N-Trifluoroacetyldoxorubicin 14-valerate ad32 N-Trifluoroacetyladriamycin 14-valerate Valstar (2S-cis)-Pentanoic Acid 2-(1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-((2,3,6-trideoxy-3-((trifluoroacetyl)amino)-a-L-lyxo-hexopyranosyl)oxy)-2-naphthacenyl)-2-oxoethyl Ester N-trifluoroacetyldoxorubicin-14-valerate antibioticad32

Description	Valrubicin is a chemotherapy agent, inhibits TPA- and PDBu-induced PKC activation with IC50s of 0.85 and 1.25 μM, respectively, and has antitumor and antiinflammatory activity.
Related Catalog	Signaling Pathways >> Epigenetics >> PKC Signaling Pathways >> TGF-beta/Smad >> PKC Research Areas >> Cancer Research Areas >> Inflammation/Immunology
Target	TPA-activated PKC:0.85 μM (IC50) PDBu-activated PKC:1.25 μM (IC50)
In Vitro	Valrubicin (AD 32) is a chemotherapy agent, inhibits TPA- and PDBu-induced PKC activation with IC50s of 0.85 and 1.25 μM, respectively. Valrubicin inhibits the binding of [3H]PDBu to PKC. Therefore, Valrubicin competes with the tumor promoter for the PKC binding site and prevents the latter from both interacting with the phospholipid and binding to PKC[1]. Valrubicin shows cytotoxic activity against squamous cell carcinoma (SCC) cell line colony formation, with IC50s and IC90s of 8.24 ± 1.60 μM and 14.81 ± 2.82 μM for UMSCC5 cells, 15.90 ± 0.90 μM, 29.84 ± 0.84 μM for UMSCC5/CDDP‡ cells, and 10.50 ± 2.39 μM, 19.00 ± 3.91 μM for UMSCC10b cells, respectively. Moreover, Valrubicin in combination with radiation enhances the cytotoxicity[2].
In Vivo	Valrubicin (3, 6, or 9 mg) reduces tumor growth at week 3 by intratumoral jection in hamster. Valrubicin (6 mg) combined with minimally cytotoxic irradiation (150, 250, or 350 cGy) causes significant tumor shrinkage in hamster[2]. Valrubicin (0.1 μg/μL) significantly reduces the number of infiltrating neutrophils in biopsies challenged with TPA at 24 h and attenuates chronic inflammation in mice. Valrubicin also decreases the expression levels of inflammatory cytokines in the acute model[3].
Cell Assay	UMSCC5 cells exposed to Valrubicin (2 μM for 3 h), a single dose of radiation (400 cGy), or the combined treatment are cultured for a further 12, 24, or 48 hours. At these times, the cells are collected by trypsinization (0.25%), washed in phosphate-buffered saline (PBS), and fixed at 5 × 106 cells/mL with 95% ethanol. Cells are incubated with ribonuclease (50 μg; 70-90 Kunitz units/mg for 30 min), and the resulting pellet resuspended in and incubated with propidium iodide (0.05 mg/mL for 10 min). The DNA content of the samples is determined by flow cytometry according to standard technique[2].
Animal Admin	Hamsters[2] Hamsters with cheek pouch tumors of 100 mm2 are randomly assigned to one of five treatment groups. Momentarily anesthetized animals each receives once a week × 3 injections (27 g × 0.5-inch needle: 0.1 mL administered slowly to the base of the lesion) of Valrubicin (3, 6, or 9 mg) or drug vehicle (Cremophor: alcohol;1:1 by volume; NCl diluent 12). A further group of animals receives anesthesia but no direct tumor treatment (control). Individual tumor sizes are measured with calipers at weekly intervals for 4 weeks, at which time the animals are sacrificed[2].
References	[1]. Chuang LF, et al. Activation of human leukemia protein kinase C by tumor promoters and its inhibition by N-trifluoroacetyladriamycin-14-valerate (AD 32). Biochem Pharmacol. 1992 Feb 18;43(4):865-72. [2]. Wani MK, et al. Rationale for intralesional valrubicin in chemoradiation of squamous cell carcinoma of the head and neck. Laryngoscope. 2000 Dec;110(12):2026-32. [3]. Hauge E, et al. Topical valrubicin application reduces skin inflammation in murine models. Br J Dermatol. 2012 Aug;167(2):288-95.

Density	1.5±0.1 g/cm3
Boiling Point	867.7±65.0 °C at 760 mmHg
Melting Point	116-117ºC
Molecular Formula	C₃₄H₃₆F₃NO₁₃
Molecular Weight	723.644
Flash Point	478.6±34.3 °C
Exact Mass	723.213867
PSA	215.22000
LogP	6.31
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.619
Storage condition	2-8℃
Water Solubility	insoluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AV9850000

CHEMICAL NAME :: Adriamycin, trifluoroacetyl-, 14-valerate

CAS REGISTRY NUMBER :: 56124-62-0

LAST UPDATED :: 199512

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C34-H36-F3-N-O13

MOLECULAR WEIGHT :: 723.71

WISWESSER LINE NOTATION :: L E6 C666 BV MVT&&&J DQ HV1Q HOVXFFF KOV4 RO1 FO- BT6OTJ DZ EQ F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 109 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 480 mg/kg/4D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 360 mg/kg/4W-I

TOXIC EFFECTS :: Cardiac - cardiomyopathy including infarction Related to Chronic Data - death

TYPE OF TEST :: DNA damage

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 14 umol/L

REFERENCE :: CBINA8 Chemico-Biological Interactions. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1969- Volume(issue)/page/year: 32,331,1980

Hazard Codes	Xi
Risk Phrases	R36/37/38
Safety Phrases	26-37/39
RIDADR	NONH for all modes of transport

26295-56-7 structure

26295-56-7

5873-43-8 structure

5873-43-8

~%

56124-62-0 structure

56124-62-0

Literature: RSC Advances, , vol. 3, # 45 p. 22963 - 22966

Precursor 2
26295-56-7 5873-43-8
DownStream 0