4720-09-6 Usage
Description
ANDROMEDOTOXIN is a tetracyclic diterpenoid, specifically a grayanotoxane derivative, with a unique chemical structure featuring a pro-R hydrogen at position 14 substituted by an acetoxy group and hydroxy groups at the 3beta-, 5-, 6beta-, 10-, and 16positions. It is derived from Fructus Rhododendri (ba li ma), the dried fruit of Rhododendron molle (Bl.) G. Don (yánɡ zhí zhú), which is primarily found in the Jiangsu, Hubei, and Jiangxi Provinces of China. ANDROMEDOTOXIN is known for its medicinal properties, such as its effectiveness in treating waist pain, arm pain, and poisoning, as well as its ability to lower blood pressure and slow the heart rate. However, it is crucial to note that a large dosage can be lethal. Physically, ANDROMEDOTOXIN appears as a white crystalline or powder substance, with a melting point of 265–268 °C and a specific optical rotation ranging from +50 to +60°. It is soluble in water, acetone, and chloroform, but almost insoluble in diethyl ether or petroleum ether.
Uses
1. Used in Traditional Medicine:
ANDROMEDOTOXIN is used as a traditional medicinal compound for treating various ailments, such as waist pain, arm pain, and poisoning. Its application in traditional medicine is attributed to its ability to lower blood pressure and slow the heart rate.
2. Used in Pharmaceutical Formulations:
ANDROMEDOTOXIN is utilized in the development of pharmaceutical formulations, including injections and tablets, due to its medicinal properties. However, it is essential to exercise caution with dosages, as high amounts can lead to severe side effects or even death.
3. Used in Cardiovascular Applications:
ANDROMEDOTOXIN is employed as a cardiovascular agent for its blood pressure-lowering and heart rate-slowing effects. Its use in this application is due to its direct impact on the cardiovascular system.
4. Used with Caution in Pregnant Women:
ANDROMEDOTOXIN should be used with caution in pregnant women, as its effects on the developing fetus are not well understood and could potentially lead to complications.
5. Used in Research and Development:
ANDROMEDOTOXIN serves as a valuable compound in the research and development of new drugs and therapies, particularly in the fields of traditional medicine and cardiovascular health. Its unique chemical structure and properties make it an interesting candidate for further study and potential applications.
History
Because rhomotoxin can slow down heart rhythm and blood pressure, Deng Dao ji
et al. from the First Affiliated Hospital of Wuhan Medical College researched
Fructus Rhododendri in the early 1970s. They extracted the crystallization from
fruits and obtained preliminary results by animal testing and clinical application .Rhomotoxin is a white needle crystal that is extracted from the dried fruit of
Rhododendron molle (Bl.) G. Don (yánɡ zhí zhú). Its biological activity is closely
related to three-dimensional specificity and hydrophobicity. 5β-hydroxyl, 6β-
hydroxyl, and, especially, the 2,3-epoxy groups can affect its biological activity .Rhomotoxin was acetylated to obtain monoacetate (Japanese Rhododendron II).
The melting points of rhomotoxin and Japanese Rhododendron III are identical
(284–286 °C). IR and Rf of silica gel thin layer chromatography are identical.
Therefore, rhomotoxin is Japanese Rhododendron III .
Pharmacology
The pharmacological effects of rhomotoxin are mainly displayed in three aspects:
(1) analgesic effect: the suspension, infusion, and alcohol made of rhomotoxin fruit
have an analgesic effect in mice ; (2) effects on cardiovascular system: the resting
heart rate is a bad prognostic indicator of hypertension and other cardiovascular
diseases. Rhomotoxin can reduce the resting heart rate; (3) kidney protection: rhomotoxin
promotes good blood pressure and a slow heart rate and provides kidney
protection. Its mechanism may be related to a reduction in the content of angiotensin
II (Ang II), increasing endothelial nitric oxide synthase (eNOS) content, and
slowing heart rate .The plasma concentration of mice decreased rapidly over time following intravenous
injection of rhomotoxin; there was no residue after 6 h. Rhomotoxin is rapidly
distributed to various organs through the blood circulation and reaches a peak within
5–15 min. The gallbladder (including bile) contained the highest amount, followed
by the liver and kidneys. It affects, in order, the gallbladder (including bile), liver,
kidney, thyroid, stomach, adrenal gland, heart, lungs, and brain. Rhomotoxin is
excreted mainly by the kidney and digestive tract. More prototype drugs are in the
urine than in the stool. Rhomotoxin has a stimulating effect on the stomach. A certain
amount of rhomotoxin also entered the thyroid and adrenal glands. A very small
amount was found in brain tissue, demonstratinge that rhomotoxin does not easily
pass through the blood-brain barrier. Plasma dialysis showed that the plasma protein
binding rate of rhomotoxin can reach as high as 60% in 30 min .
Clinical Use
Rhomotoxin acts as an antihypertensive drug, and it is able to lower the blood pressure
in patients with severe hypertension. Its pharmacological effects are related to
parasympathetic function. Large-dosage-induced low blood pressure can be restored
with ephedrine. Its antihypertensive effect lasts for 0.5–1 h. If blood pressure has
not dropped to a satisfactory level, rhomotoxin must not have been added because
an excessive drop in blood pressure would lead to shock. Oral administration with
aluminum hydroxide can reduce rhomotoxin-induced stomach discomfort.
Intramuscular injection can also cause local pain. In addition, procaine reduces its
antihypertensive effect. Secondary hypertension and malignant hypertension
patients should use it with caution, critical and dying patients should be disabled
(including, for example, severe heart failure, cardiomyopathy, atrioventricular
block, and severe ventricular arrhythmias).
Safety Profile
Poison by subcutaneous,parenteral, intravenous and intraperitoneal routes. Whenheated to decomposition it emits acrid smoke and fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 4720-09-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,2 and 0 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 4720-09:
(6*4)+(5*7)+(4*2)+(3*0)+(2*0)+(1*9)=76
76 % 10 = 6
So 4720-09-6 is a valid CAS Registry Number.
InChI:InChI=1/C22H36O7/c1-11(23)29-17-12-6-7-13-20(5,27)14-8-15(24)18(2,3)22(14,28)16(25)9-21(13,17)10-19(12,4)26/h12-17,24-28H,6-10H2,1-5H3/t12?,13-,14-,15-,16+,17+,19+,20+,21?,22-/m0/s1
4720-09-6Relevant articles and documents
Studies on the Constituents of the Leaves of Pieris japonica D. Don
Katai, Masaaki,Fujiwara, Masayoshi,Terai, Tadamasa,Meguri, Haruo
, p. 3124 - 3126 (2007/10/02)
Four new diterpenoids, pieristoxins H(I), I(II), J(III) and K(IV), were isolated from the leaves of Pieris japonica D.Don, together with the known diterpenoids, asebotoxin IV(XI) and VII(XII).The chemical structures of I and II were established to be 7-O-hydroxy and 14-O-lactoyl grayanotoxin III, respectively.III and IV were shown to be esters of pieristoxin G(VI), one of the most highly oxygenated grayanoids.Keywords---Pieris japonica; Ericaceae; asebi; diterpenoids; pieristoxin H; pieristoxin I; pieristoxin J; pieristoxin K; grayanoid; toxin