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Ipriflavone

Ipriflavone structure

CAS No:
35212-22-7
Formula:
C18H16O3
Chemical Name:
Ipriflavone
Synonyms:
4H-1-Benzopyran-4-one,7-(1-methylethoxy)-3-phenyl-;7-(1-Methylethoxy)-3-phenyl-4H-1-benzopyran-4-one;7-Isopropoxyisoflavone;Ipriflavone;FL 113;7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one;TC 80;Osteofix;Osteofix (pharmaceutical);Osten;Yambolap;Iprosten;TC 80 (pharmaceutical);Iprivone;3-Phenyl-7-propan-2-yloxychromen-4-one
Categories:
Active Pharmaceutical Ingredients > Fluid, Electrolyte, and Acid-base Balance

Description

Ipriflavone is a synthetic isoflavone derivative used to suppress bone resorption.

Solid

Ipriflavone is a member of the class of isoflavones that is isoflavone in which the hydrogen at position 7 is replaced by an isopropoxy group. A synthetic isoflavone, it was formerly used for the treatment of osteoporosis, although a randomised controlled study failed to show any benefit. It is still used to prevent osteoporosis in post-menopausal women. It has a role as a bone density conservation agent. It is a member of isoflavones and an aromatic ether.

Ipriflavone Basic Attributes

Molecular Weight：

280.32

Exact Mass：

280.32

EC Number：

201-641-0

UNII：

80BJ7WN25Z

DSSTox ID：

DTXSID5040679

ATC Code：

M - Musculo-skeletal system

HScode：

2914509090

Characteristics

PSA：

35.5

XLogP3：

Appearance：

Solid

Density：

1.2±0.1 g/cm3

Melting Point：

115-117 °C

Boiling Point：

435.9°C at 760 mmHg

Flash Point：

209.3±15.1 °C

Refractive Index：

1.592

Water Solubility：

2.301 mg/L @ 25 °C (est)

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Collision Cross Section：

164.3 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

24/25-36/37/39-27-26

RTECS Number：

DJ3100500

Marks：

Drug Information

Metabolism/Metabolites：

Ipriflavone has known human metabolites that include 3-Phenyl-7-(1-methyl-2-hydroxyethoxy)-4H-1-benzopyran-4-one, 4H-1-Benzopyran-4-one, 3-(4-hydroxyphenyl)-7-(1-methylethoxy)-, and 7-Hydroxyisoflavone.

MeSH Entry Terms：

7-isopropoxyisoflavone

Ipriflavone Use and Manufacturing

Methods of Manufacturing

To a solution of 2.50 g of analog 1 (10.5 mmol) in 30 ml of DMF was added 1.80 g of anhydrous IL2CO3 (13.0 mmol) and 3.0 ml of 2-bromopropane (32.0 mmol). The mixture was stirred at 80 °C for 4 hours and then poured into ice water. Precipitates were collected by filtration, washed with small portions of water, and dried to give a residue of crude product. The residue was loaded onto a Sephadex LH-20 column (chloroform : methanol, 7: 3) and fractions that contained pure product were pooled, concentrated, and recrystallized from acetone to give 1.05 g of crystalline analog 5, a yield of 42 percent (w/w): mp 110-111 °C. 1H NMR (DMSO-d6) 8 1.33 (-CH3), 1.34 (-CH3), 4.86 (m, 1H, >CH2-), 7.05 (dd, 1H, J= 8. 86, 2.20 Hz, 6-H), 7.16 (d, 1H, J= 2. 50 Hz, 8H), 7.38 (t, 1H, J= 6.78 Hz, 4'-H), 7.44 (t, 2H, J= 7.76, 1.6 Hz, 3', 5'-H), 7.59 (d, 2H, J= 8.09, 1.6 Hz, 2', 6'-H), 8. 02 (d, IH, J= 8. 86 Hz, 5-H), 8. 46 (s, 1H, 2-H). 13C NMR (DMSO-d6) 8 21.5 (-CH3), 21.5 (-CH3), 70.4 (-CH2-O-), 101. 8 (C-8), 115.7 (C-6), 117.3 (C-10), 123.7 (C-3), 127.0 (C-1'), 127.8 (C-5), 128.1 (C-3', 5'), 128.9 (C-2', 6'), 132.0 (C4'), 154.0 (C-2), 157.5 (C-9), 162.0 (C-7), 174.1 (C-4). MS (m/z) 281.4 (M + H) +, 303. 3 (M + Na) +, 319.4 (M + K) +, 279.5 (M-H)-. Anal. (C23H2405) for C, H. Cacld : 77.12, 5.75 ; found: 76.50, 5.69.

Uses

anabolic It acts directly on the bone, inhibits bone resorption, and increases the secretion of calciferin through estrogen. Used for osteoporosis and bone loss. Hormonal drugs.

Computed Properties

Molecular Weight:280.3
XLogP3:4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:280.109944368
Monoisotopic Mass:280.109944368
Topological Polar Surface Area:35.5
Heavy Atom Count:21
Complexity:407
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Resorcinol

Potassium carbonate

Acetic acid

Zinc chloride

Drug Function and Efficacy

It is used to improve osteoporosis-induced bone loss, and has an inhibitory effect on experimental osteoporosis rats caused by ovariectomy and prednisolone. Its mechanism of action includes: directly inhibiting bone resorption; increasing the secretion of calcitonin through estrogen-like effects, indirectly producing an anti-bone resorption effect; and promoting bone formation.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Ipriflavone tablets
Ingredients	The main ingredient of this product is ipriflavone. Chemical name: 7-isopropoxy-3-phenyl-4H-1-benzopyran-4-one.
Indication	1. For animals with ovaries removed, the use of estrone can enhance the effect of estrogen, so caution should be exercised when using this drug with estrogen preparations. 2. Theophylline can increase the blood concentration of theophylline when used together, so the dosage of theophylline should be reduced and caution should be exercised when using this drug with theophylline. 3. Coumarin anticoagulants can enhance the effect of coumarin anticoagulants, so the dosage of coumarin anticoagulants should be reduced and caution should be exercised when using this drug with anticoagulants.
Specifications	0.2g

Ipriflavone tablets
Ingredients	The ingredient is ipriflavone.
Indication	Not yet clear
Specifications	0.2g
Manufacturer	Shanghai Sine Tianping Pharmaceutical Co., Ltd.

Ipriflavone
Manufacturer	Chifeng Arker Pharmaceutical Technology Co., Ltd.

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Registered Holders

Chifeng Arker Pharmaceutical Technology Co., Ltd.

China
Active
Hubei Sihuan Pharmaceutical Co., Ltd.

China
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