DOXO-EMCH - CAS 151038-96-9

DOXO-EMCH - CAS 151038-96-9 Catalog number: BADC-00028

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DOXO-EMCH is an albumin-binding prodrug of doxorubicin, which is an anthracycline antibiotic with anti-Gram-positive bacterial activity and a broad antitumor spectrum.

ADCs Cytotoxin
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Ordering Information

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BADC-00028 -- $--
DOXO-EMCH is an albumin-binding prodrug of doxorubicin, which is an anthracycline antibiotic with anti-Gram-positive bacterial activity and a broad antitumor spectrum.
1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, [1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-hydroxyethylidene]hydrazide; 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, [1-[4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-hydroxyethylidene]hydrazide, (2S-cis)-; Doxorubicin-EMCH
Canonical SMILES
1.60±0.1 g/cm3
Soluble in DMSO
In Vitro
The LD50 of DOXO-EMCH was >60 mg/kg doxorubicin equivalents in both male and female mice (the LD50 of doxorubicin in CD-1 mice is -12 mg/kg). In Sprague-Dawley rats, the LD50 was 23.4 and 45.9 mg/kg doxorubicin equivalents for males and females, respectively.
In Vivo
In Beagle dogs, LD10 was not reached for DOXO-EMCH at 4.5 mg/kg doxorubicin equivalents. A four-cycle intravenous study with DOXO-EMCH at dose levels of 4 x 2.5, 5.0 or 7.5 mg/kg doxorubicin equivalents in rats revealed approximately three-fold less side effects on the hemolymphoreticular system when compared to 4 x 2.5 mg/kg doxorubicin dose, whereas effects on the testes/oligospermia seem to be comparable between both drugs at equitoxic dose. The toxicity studies with DOXO-EMCH in mice, rats or dogs have not identified any other special toxicity when compared to the toxicity data for doxorubicin. Preclinical tolerance of DOXO-EMCH was higher in mice, rats and dogs compared to doxorubicin. A dose of 20 mg/m2 doxorubicin equivalents was recommended as the starting dose for a phase I study with DOXO-EMCH.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT02029430Kaposi's SarcomaPhase 22016-10-19CytRxCompleted
NCT01337505Malignant Solid TumourPhase 12013-02-13CytRxCompleted
NCT02235688Metastatic Solid TumorsPhase 12017-06-07CytRxCompleted
NCT02014844GlioblastomaPhase 22017-01-06CytRxCompleted
NCT01673438Advanced Solid TumorPhase 12014-04-21CytRxCompleted
ADCs Cytotoxin-Linker
Red solid powder
Shelf Life
≥360 days if stored properly
Room temperature, or blue ice upon request.
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Current Developer
Innovive Pharmaceuticals and CytRx Corporation
1.A phase 1B/2 study of aldoxorubicin in patients with soft tissue sarcoma.
Chawla SP1, Chua VS, Hendifar AF, Quon DV, Soman N, Sankhala KK, Wieland DS, Levitt DJ. Cancer. 2015 Feb 15;121(4):570-9. doi: 10.1002/cncr.29081. Epub 2014 Oct 13.
BACKGROUND: Aldoxorubicin, a prodrug of doxorubicin, covalently binds to serum albumin, allowing for the administration of much higher doses of doxorubicin in a previous clinical study. The current phase 1B/2 study evaluated the safety of aldoxorubicin, including preliminary efficacy and safety of its maximum tolerated dose (MTD).
2.Therapeutic efficacy of aldoxorubicin in an intracranial xenograft mouse model of human glioblastoma.
Marrero L1, Wyczechowska D2, Musto AE3, Wilk A2, Vashistha H2, Zapata A2, Walker C2, Velasco-Gonzalez C4, Parsons C2, Wieland S5, Levitt D5, Reiss K2, Prakash O2. Neoplasia. 2014 Oct 23;16(10):874-82. doi: 10.1016/j.neo.2014.08.015. eCollection 2014.
Glioblastoma multiforme (GBM) is the most aggressive primary brain tumor with a median survival of 12 to 15 months after diagnosis. Acquired chemoresistance, high systemic toxicity, and low penetration of the blood brain barrier by many anticancer drugs contribute to the failure of anti-GBM therapies. To circumvent some of these obstacles, we tested a novel prodrug approach to evaluate anti-GBM efficacy by utilizing serum albumin-binding doxorubicin (Doxo), aldoxorubicin (Aldoxo), which is less toxic, is released from albumin in an acidic environment and accumulates in tumor tissues. A human GBM cell line that expresses a luciferase reporter (U87-luc) was stereotactically injected into the left striatum of the brain of immunodeficient mice. Following initial tumor growth for 12 days, mice were injected once a week in the tail-vein with Aldoxo [24 mg/kg or 18 mg/kg of doxorubicin equivalents-3/4 maximum tolerated dose (MTD)], Doxo [6 mg/kg (3/4 MTD)], or vehicle.
3.First-Line Aldoxorubicin vs Doxorubicin in Metastatic or Locally Advanced Unresectable Soft-Tissue Sarcoma: A Phase 2b Randomized Clinical Trial.
Chawla SP1, Papai Z2, Mukhametshina G3, Sankhala K4, Vasylyev L5, Fedenko A6, Khamly K7, Ganjoo K8, Nagarkar R9, Wieland S10, Levitt DJ10. JAMA Oncol. 2015 Dec;1(9):1272-80. doi: 10.1001/jamaoncol.2015.3101.
IMPORTANCE: Standard therapy for advanced soft-tissue sarcoma has not changed substantially in decades, and patient prognosis remains poor. Aldoxorubicin, a novel albumin-binding prodrug of doxorubicin, showed clinical activity against advanced soft-tissue sarcoma in phase 1 studies.
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