Calanolide A
Scientific Name(s): Calophyllum lanigerum var. austrocoriaceum
Common Name(s): Calanolide A
Medically reviewed by Drugs.com. Last updated on Sep 23, 2024.
Clinical Overview
Use
Calanolide has demonstrated antimicrobial and antiviral activities, with interest focused on applications in HIV; however, clinical trial data are lacking to support use for any indication.
Dosing
Clinical data are lacking to provide dosing recommendations for C. lanigerum or its extracts.
Contraindications
Contraindications have not been identified.
Pregnancy/Lactation
Avoid use. Information regarding safety and efficacy in pregnancy and lactation is lacking.
Interactions
None well documented.
Adverse Reactions
Because calanolide A is a relatively new product, data are limited regarding potential adverse reactions.
Toxicology
No data.
Scientific Family
- Clusiaceae (Mangosteen)
Botany
The tree C. lanigerum var. austrocoriaceum grows in the rain forest of the Malaysian state of Sarawak on the island of Borneo. There are at least 200 species in the genus Calophyllum.(McKee 1998, Shenon 1994, USDA 2021) The calanolide A component is isolated from the latex.
History
In 1987, an Illinois team of scientists contracted by the National Cancer Institute (NCI) to search for natural drugs in tropical rain forests obtained specimen samples from various rain forest trees, one of which was C. lanigerum. Four years later, the NCI discovered that a preparation from this gum tree was active against HIV-1.(Defant 2015, Nahar 2020, Shenon 1994) In 2016, Craun Research announced that phase 1 trials with calanolide A had been completed. In 2017, F18, a synthetic structural analog of calanolide A, demonstrated more potent anti-HIV activity than calanolide A.(Nahar 2020)
Chemistry
Plants from the genus Calophyllum have been shown to contain xanthones, steroids, triterpenes, coumarins, and benzopyrans. Calanolide A is an 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:20,30-h]chromen-2-one substituted by a hydroxyl (–OH) group at C-12; methyl groups at positions 6, 6, 10, and 11; and a propyl group at C-4. It is considered a dipyranocoumarin, with nonnucleoside HIV-1–specific reverse transcriptase–inhibiting properties.(McKee 1996, McKee 1998, Nahar 2020) Its molecular formula is C22H26O5.(Nahar 2020) Many studies of the genus Calophyllum include findings regarding structural representations, related compounds and their derivatives, and modifications of the molecule.(Galinis 1996, Kashman 1992, Ma 2008, McKee 1996, McKee 1998, Sekino 2004, Yu 2007, Zembower 1997) Calanolide A has been synthesized in the lab and was found to have similar actions to the natural product.(Flavin 1996) Calanolides are among the first plant-based compounds to show activity against HIV-1.(Nahar 2020)
Uses and Pharmacology
Antimicrobial activity
In vitro data
An in vitro study investigated the activity of modified calanolides against Mycobacterium tuberculosis.(Liu 2015)
Antiviral activity
Early interest persists in using Calophyllum extracts in the management of HIV infections,(Matthée 1999, Newman 1998) particularly for clinically relevant mutant HIV strains.(Usach 2013) Calanolide A and related compounds from the genus Calophyllum have demonstrated antiviral activity, including nonnucleoside reverse transcriptase inhibition(Matthée 1999, Newman 1998) and activity against influenza H3N1 and H1N1 viruses.(Rajasekaran 2013)
Animal and in vitro data
Calanolide A has demonstrated synergistic effects with other anti-HIV drugs in cell and animal models.(Nahar 2020)
Clinical data
Published clinical research on C. lanigerum is lacking. Calanolide A has been investigated in phase 1 clinical trials to evaluate safety, tolerability, and pharmacokinetics.(Creagh 2001, Usach 2013) In 2016, Craun Research announced that phase 1 trials with calanolide A had been completed.(Nahar 2020)
Cancer
Calanolide A is being investigated as an antitumor agent.(Defant 2015, Nahar 2020)
Dosing
Clinical data are lacking to provide dosing recommendations for C. lanigerum or its extracts.
Calanolide A is an investigational anti-HIV drug that has been evaluated in early phase 1 single-dose safety and pharmacokinetic clinical trials in healthy subjects (oral dose range, 200 to 800 mg); however, safety and efficacy remain to be defined, and calanolide A is not available for use.(Creagh 2001, Nahar 2020)
Calanolides are associated with high safety margins and favorable pharmacokinetic profiles; while several analogues of the naturally occurring calanolides have been synthesized, further research is required to commercially bring any of the calanolide candidates, natural or synthetic, to the anti-HIV drug market.(Nahar 2020)
Pregnancy / Lactation
Avoid use. Information regarding safety and efficacy in pregnancy and lactation is lacking.
Interactions
None well documented.
Adverse Reactions
Because calanolide A is a relatively new product, data are limited regarding potential adverse reactions. An early phase 1 single-dose safety and pharmacokinetic clinical trial in healthy subjects demonstrated a favorable safety profile.(Creagh 2001, Usach 2013)
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Toxicology
Information is limited. Animal studies demonstrated that oral calanolide A is generally well tolerated in doses of up to 150 mg/kg in rats and 100 mg/kg in dogs. In a study of healthy patients without HIV, there were no serious or toxic effects with calanolide A use.(Nahar 2020)
References
Disclaimer
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Further information
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