Page last updated: 2024-12-07

annamycin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Annamycin is an anthracycline antibiotic that was first isolated from the bacterium Streptomyces galilaeus. It exhibits potent antitumor activity against a variety of cancer cell lines. It is known to intercalate into DNA, inhibiting DNA replication and transcription. Annamycin's unique mechanism of action makes it a promising candidate for the treatment of certain types of cancers, particularly those resistant to other chemotherapy drugs. Annamycin's synthesis involves a complex series of enzymatic reactions that have been extensively studied, and its structure-activity relationship has been investigated to develop analogs with improved therapeutic profiles.'

annamycin: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID115212
SCHEMBL ID19368
MeSH IDM0214612

Synonyms (13)

Synonym
annamycin
ar-522
2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin
5,12-naphthacenedione, 7-((2,6-dideoxy-2-iodo-alpha-l-mannopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7s-cis)-
92689-49-1
(7s,9s)-7-[(2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7h-tetracene-5,12-dione
unii-snu299m83q
snu299m83q ,
SCHEMBL19368
Q4767903
DB06420
(7s,9s)-7-(((2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione
DTXSID901027238

Research Excerpts

Overview

Annamycin (Ann) is a non-cross-resistant lipophilic anthracycline antiobiotic optimally suited for liposome delivery. Annamycin is being developed for clinical studies formulated in liposomes.

ExcerptReferenceRelevance
"Annamycin is a highly lipophilic form of the anthracycline doxorubicin with the ability to bypass multidrug resistance mechanisms of cellular drug resistance."( Phase I/II trial of nanomolecular liposomal annamycin in adult patients with relapsed/refractory acute lymphoblastic leukemia.
Andreeff, M; Ford, LA; Heffner, TL; Kantarjian, HM; O'Brien, S; Parekh, S; Shepard, R; Thomas, DA; Wang, ES; Wetzler, M, 2013
)
1.37
"Annamycin (Ann) is a non-cross-resistant lipophilic anthracycline antiobiotic optimally suited for liposome delivery. "( Effect of vesicle size and lipid composition on the in vivo tumor selectivity and toxicity of the non-cross-resistant anthracycline annamycin incorporated in liposomes.
Ling, YH; Perez-Soler, R; Priebe, W; Reddy, S; Zou, Y, 1995
)
1.94
"Annamycin (AN) is an anthracycline antibiotic with high affinity for lipid membranes which is being developed for clinical studies formulated in liposomes. "( In vitro cytotoxicity, cellular pharmacology, and DNA lesions induced by annamycin, an anthracycline derivative with high affinity for lipid membranes.
Burke, TG; Ling, YH; Perez-Soler, R; Pommier, Y; Priebe, W; Yang, LY, 1993
)
1.96
"Annamycin (Ann) is a lipophilic, non-cross resistant anthracycline antibiotic that is easily amenable to formulation in a wide variety of liposomal carriers. "( Organ distribution and tumor uptake of annamycin, a new anthracycline derivative with high affinity for lipid membranes, entrapped in multilamellar vesicles.
Ling, YH; Perez-Soler, R; Priebe, W; Zou, Y, 1993
)
2
"Annamycin (Ann) is a lipophilic and non-cross-resistant anthracycline antibiotic currently in clinical development as a liposomal formulation (L-Ann) composed of dimyristoylphosphatidylcholine (DMPC) and dimyristoylphosphatidylglycerol (DMPG). "( Distribution of free and liposomal annamycin within human plasma is regulated by plasma triglyceride concentrations but not by lipid transfer protein.
Perez-Soler, R; Wasan, KM, 1995
)
2.01
"Annamycin (Ann) is a highly lipophilic anthracycline antibiotic that has been shown to circumvent MDR-1 both in vitro and in vivo. "( Annamycin circumvents resistance mediated by the multidrug resistance-associated protein (MRP) in breast MCF-7 and small-cell lung UMCC-1 cancer cell lines selected for resistance to etoposide.
Andreeff, M; Doyle, LA; Ling, YH; Neamati, N; Perez-Soler, R; Priebe, W; Schneider, E; Zou, Y, 1997
)
3.18
"Annamycin (Ann) is a new lipophilic anthracycline antibiotic with a marked ability to circumvent typical multidrug resistance both in vitro and in vivo. "( Preclinical toxicity of liposome-incorporated annamycin: selective bone marrow toxicity with lack of cardiotoxicity.
Perez-Soler, R; Priebe, W; Stephens, LC; Zou, Y, 1995
)
1.99
"Annamycin is a highly lipophilic anthracycline with the ability to bypass the MDR-1 mechanism of cellular drug resistance. "( Phase I study of liposomal annamycin.
Booser, DJ; Cossum, P; Esparza-Guerra, L; Hortobagyi, GN; Perez-Soler, R; Priebe, W; Wu, QP; Zou, Y, 2000
)
2.05
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's18 (72.00)18.2507
2000's6 (24.00)29.6817
2010's1 (4.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.59

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.59 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index4.11 (4.65)
Search Engine Demand Index45.55 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.59)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (10.34%)5.53%
Reviews3 (10.34%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (79.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (8)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Phase 1/2 Study of Liposomal Annamycin for the Treatment of Subjects With Acute Myeloid Leukemia (AML) That is Refractory to or Relapsed After Induction Therapy [NCT03388749]Phase 1/Phase 220 participants (Actual)Interventional2018-12-17Completed
Phase 1B/2 Study Of Liposomal Annamycin (L-Annamycin) In Subjects With Previously Treated Soft-Tissue Sarcomas With Pulmonary Metastases [NCT04887298]Phase 1/Phase 236 participants (Actual)Interventional2021-06-05Active, not recruiting
Phase 1b/2 Study of Liposomal Annamycin (L-Annamycin) in Subjects With Previously Treated Soft-Tissue Sarcomas (STS) With Pulmonary Metastases (ANNA-SARC) [NCT05518526]Phase 1/Phase 264 participants (Anticipated)Interventional2022-08-23Recruiting
Phase 1/2 Study of Liposomal Annamycin in Combination With Cytarabine for the Treatment of Subjects With Acute Myeloid Leukemia (AML) [NCT05319587]Phase 1/Phase 263 participants (Anticipated)Interventional2022-09-29Recruiting
Phase 1/2 Study of Liposomal Annamycin for the Treatment of Subjects With Acute Myeloid Leukemia (AML) That is Refractory to or Relapsed After Standard Induction Therapy [NCT03315039]Phase 1/Phase 27 participants (Actual)Interventional2018-03-28Completed
Phase I Study of Liposomal Annamycin in Children and Young Adults With Refractory or Relapsed Acute Lymphocytic Leukemia and Acute Myelogeneous Leukemia [NCT00430443]Phase 13 participants (Actual)Interventional2007-02-28Terminated(stopped due to Participants are no longer being examined or treated.)
Phase I/II Study of Liposomal Annamycin in Patients With Refractory or Relapsed Acute Lymphocytic Leukemia [NCT00271063]Phase 1/Phase 234 participants (Anticipated)Interventional2005-10-31Recruiting
Phase I/II Clinical and Pharmacological Study of Liposomal Annamycin in Anthracycline-Resistant Breast Cancer [NCT00012129]Phase 1/Phase 20 participants Interventional1998-09-30Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT03315039 (3) [back to overview]Dose-limiting Toxicity
NCT03315039 (3) [back to overview]Number of Participants With Anti-leukemic Activity
NCT03315039 (3) [back to overview]Pharmacokinetics - Area Under the Plasma Concentration

Dose-limiting Toxicity

Number of patients with a dose-limiting toxicity (DLT) at each dose evaluated (NCT03315039)
Timeframe: Day 28

InterventionParticipants (Count of Participants)
Dose Level 1: 100 mg/m2/Day Liposomal Annamycin0
Dose Level 2 : 120 mg/m2/Day Liposomal Annamycin0

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Number of Participants With Anti-leukemic Activity

Determined by acute myeloid leukemia (AML) response rate based on the International Working Group (IWG) Response Criteria in AML (Cheson, 2003). Anti-leukemic Activity measured by bone marrow biopsy/aspirate pre and post treatment. (NCT03315039)
Timeframe: 15-35 Days after the start of therapy

,
InterventionParticipants (Count of Participants)
Morphological Leukemia Free State (MLFS)Treatment Failure (TF)
100 mg/m204
120 mg/m212

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Pharmacokinetics - Area Under the Plasma Concentration

Area under the plasma concentration - time curve (AUC) of annamycin and its metabolite, annamycinol (NCT03315039)
Timeframe: Pre-dose and at 0.25, 0.5, 1, 2, 4, 8, and 24 hours after the start of liposomal annamycin infusion on Day 1 and Day 3

Interventionhr*ng/ml (Geometric Mean)
Annamycin 100 mg/m2 - Day 1Annamycin 100 mg/m2 - Day 3Annamycin 120 mg/m2 - Day 1Annamycin 120 mg/m2 - Day 3Annamycinol 100 mg/m2 - Day 1Annamycinol 100 mg/m2 - Day 3Annamycinol 120 mg/m2 - Day 1Annamycinol 120 mg/m2 - Day 3
Liposomal Annamycin14301610233028801400152013701610

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